Huddle Up with Mark The Fund Coach

Why do some nonprofits struggle to grow even when their leaders are working harder than ever?

In Part 2 of The Road to a Million, Mark Duncan explores four organizational barriers that may be keeping your nonprofit stuck: limiting money mindsets, the executive director's leadership trap, reactive fundraising, and a lack of alignment between executive leadership and the board.

Discover why sustainable growth requires more than increasing your fundraising goal—and how relationship-driven major gift fundraising can help create the financial stability needed to expand your mission.

You'll also hear three practical questions to bring to your next leadership or board conversation.

Free companion resource: From Money Mindset to Mission Growth: An Organizational Action Guide.

Download the guide and take the next step toward building a sustainable million-dollar nonprofit.

Here's the Money Mindset Assessment to see your organization's Money Mindset.

What if your nonprofit had twice the financial resources it has today? How many more people could you serve? What new opportunities could you create? And what's really keeping your organization from getting there?

In this episode of Huddle Up with Mark The Fund Coach, we're kicking off a new three-part series called The Road to a Million.

Inspired by a recent coaching conversation, we're challenging nonprofit leaders to rethink the financial limitations they've accepted and imagine what greater resources could make possible for their missions.

We'll explore the difference between maintaining an organization and growing its impact, why nonprofits sometimes remain stuck at the same operating budget year after year, and how major gifts and relationship fundraising can create a pathway toward sustainable growth.

If you're leading a small or midsize nonprofit and wondering how to take your organization to the next level, this series is for you.

Because the goal isn't a million dollars. It's what a million dollars makes possible.

Subscribe to Huddle Up with Mark The Fund Coach for Parts 2 and 3 of The Road to a Million.

Subscribe to The Weekly Huddle for fundraising insights and resources: https://www.thefundcoach.com/opt-in

The Ask Is Over. Now What? How Major Gift Leaders Respond and Strengthen Donor Relationships

You've built the relationship. You've made the ask. And now the donor has responded.

What happens next? In this episode of Huddle Up with Mark The Fund Coach, Mark explores one of the most important—and often overlooked—parts of major gift fundraising: how you respond after the solicitation.

Whether a donor says yes, no, needs more time, or goes quiet, your response can strengthen or undermine the trust you've worked to build.

Discover how to navigate donor decisions with confidence, follow up respectfully, and recognize why stewardship is about more than acknowledging a gift.

Because relationship fundraising doesn't end when the ask is over.

The donor's answer matters. But how you respond matters just as much.**

Join The Weekly Huddle for more practical Major Gift Leadership insights: https://www.thefundcoach.com/opt-in

You know your donor. You've built trust. You've explored what matters to them. But when it's finally time to invite them to make a significant gift, the conversation suddenly feels uncomfortable.

In this episode of *Huddle Up with Mark The Fund Coach*, Mark explains why asking for a major gift doesn't have to feel like a sales pitch—and how Executive Directors can approach the conversation with greater confidence.

You'll discover how to connect the invitation to a donor's interests, make a clear and respectful request, give the donor space to respond, and navigate a "no" or "not yet" without jeopardizing the relationship.

Because the ask isn't about pressuring someone to give. It's about inviting them to invest in a vision they care about.

A great major gift ask doesn't interrupt the relationship. It grows out of it.

Get more practical Major Gift Leadership ideas in The Weekly Huddle: https://www.thefundcoach.com/opt-in

You know you should stay connected with your major donors. But what do you say when you’re not asking them for money?

Too often, nonprofits confuse communicating with donors with actually building relationships. Newsletters, annual reports, event invitations, and appeals all have a role—but sending more communications doesn’t necessarily create a deeper connection.

In this episode of Huddle Up with Mark The Fund Coach, Mark explores how Major Gift Leaders create meaningful donor touchpoints based on what they’ve learned about the individual donor.

You’ll learn why donor discovery should shape future interactions, how to find genuine reasons to reach out, why not every conversation needs to move someone closer to an ask, and how a simple message—“I remember what matters to you”—can communicate something far more powerful than another cultivation tactic.

Because relationship fundraising isn’t about pretending to care. It’s taking the time to actually care.

Want more practical Major Gift Leadership ideas? Join The Weekly Huddle FREE: https://www.thefundcoach.com/opt-in

Your organization needs to raise money. So the board starts asking: Who can we ask?

But if that's when you begin building relationships with prospective major donors, you've already put yourself at a disadvantage.

In this episode of Huddle Up with Mark The Fund Coach, we're exploring why Major Gift Leaders build donor relationships long before they need to ask for anything.

We'll talk about why your organization's urgency isn't necessarily your donor's urgency, how transactional fundraising creates a cycle of constantly starting over, and why genuine cultivation is about much more than waiting for the right moment to make an ask.

You'll also learn how to begin building a relationship pipeline by identifying people whose connection with your mission is worth intentionally deepening today.

Because relationships aren't what you do before the ask. Relationships are the work.

Want practical Major Gift Leadership ideas like this every week? Join The Weekly Huddle FREE: https://www.thefundcoach.com/opt-in

Major donor meetings can create a lot of pressure for nonprofit leaders. You prepare your talking points, review your programs, memorize the statistics, and try to figure out exactly what you're going to say.

But Major Gift Leaders understand that the most powerful skill in a donor conversation isn't speaking.

It's listening.

In this episode of Huddle Up with Mark The Fund Coach, we explore donor discovery and the difference between knowing about a donor and actually understanding the person behind the gift.

You'll learn how to enter donor conversations with curiosity instead of an agenda, ask questions that invite meaningful stories, and listen for the experiences, values, and aspirations that reveal what truly matters to someone.

We'll also talk about why “Tell me more” can be three of the most powerful words in relationship fundraising—and why discovery should determine the next step in a donor relationship rather than simply becoming another technique for getting to the ask.

Because your goal isn't to discover the quickest route to someone's wallet. It's to discover whether there's authentic alignment between what they care about and the change your mission is working to create.

Keep Growing as a Major Gift Leader

If this episode helped you think differently about your donor conversations, join me in The Weekly Huddle.

Each week, you'll get the latest episode of Huddle Up with Mark The Fund Coach along with practical ideas to help you build trusting donor relationships, lead major gifts with greater confidence, and become the Major Gift Leader your mission needs.

Subscribe FREE to The Weekly Huddle: https://www.thefundcoach.com/opt-in

Welcome to Season 3 of Huddle Up with Mark The Fund Coach!

Your major donor doesn't want your fundraising pitch. They don't want to sit through a presentation about your programs, your budget, or everything your organization needs. They want a conversation.

In this Season 3 premiere, we're exploring one of the most important shifts you can make as a nonprofit Executive Director: moving from pitching donors to building authentic relationships with them.

You'll learn why the best major donor conversations begin with curiosity and listening, how to ask better questions that uncover what your donors truly care about, and how to move the conversation away from organizational needs and toward meaningful possibilities for impact.

We'll also tackle an important misconception about relationship fundraising: building relationships doesn't mean avoiding the ask. It means creating enough trust, understanding, and alignment that an invitation to give becomes a natural next step.

If you've ever felt like meeting with a major donor means you have to become a salesperson, this episode will give you a different perspective.

You don't need a better pitch. You need better conversations.

That's part of becoming the Major Gift Leader your mission needs.

FREE GUIDE: 5 Habits of Executive Directors Who Land Big Gifts: https://bit.ly/4hFkOth

Connect with me on LinkedIn: https://www.linkedin.com/in/mlduncan/

To get this video podcast in your inbox, visit and subscribe here: https://www.thefundcoach.com/opt-in

Let's Talk! Click here to schedule a Major Gift Strategy Session to get clarity on what your mission needs: https://calendly.com/thefundcoach/complimentary-coaching-session

Windfall - Wealth Analytics Report: https://analytics.windfall.com/partner/the-fund-coach

Welcome to the Season 2 finale of Huddle Up with Mark The Fund Coach! Over the past season, we've talked about relationship fundraising, transformational generosity, and what it means to become the kind of leader major donors naturally want to invest in. If there's one lesson I hope you've taken away, it's this: major gifts aren't built on fundraising tactics—they're built on leadership.

As we wrap up the season, I want to focus on one of the most important leadership relationships you'll ever have as an Executive Director: your board. Too often, nonprofit leaders either expect too much from their board or not enough. The result is missed opportunities to build the kind of culture that inspires transformational generosity. In this episode, we'll explore the role your board should play in major gift fundraising, the common mistakes organizations make, and how Major Gift Leaders engage their boards as partners in building authentic donor relationships.

Thank you for being part of the Huddle Up community throughout Season 2. I truly appreciate you investing your time with me each week, and I hope these conversations have encouraged you to lead with greater confidence and purpose. We'll be taking a short break during August, but don't worry—we'll be back with Season 3 beginning September 8th, with more practical strategies, leadership insights, and conversations to help you become the Major Gift Leader your mission needs.

***NEW COHORT***

Introducing The Major Gift Leadership Cohort - exclusive 8-week coaching intensive for Executive Directors and nonprofit leaders who want to build authentic donor relationships that naturally lead to transformational gifts. Visit here to learn more: https://www.thefundcoach.com/cohort-waiting-list

FREE GUIDE: 5 Habits of Executive Directors Who Land Big Gifts: https://bit.ly/4hFkOth

Connect with me on LinkedIn: https://www.linkedin.com/in/mlduncan/

To get this video podcast in your inbox, visit and subscribe here: https://www.thefundcoach.com/opt-in

Let's Talk! Click here to schedule a Major Gift Strategy Session to get clarity on what your mission needs: https://www.thefundcoach.com/discovery-session-booking-page

Windfall - Wealth Analytics Report: https://analytics.windfall.com/partner/the-fund-coach

Most Executive Directors didn't choose their role because they wanted to become fundraisers. They accepted the responsibility because they believed in a mission worth fighting for. But at some point, every nonprofit leader discovers the same truth: if the mission is going to grow, someone has to inspire generosity—and that someone is often them.

In this episode of Huddle Up with Mark The Fund Coach, I challenge you to make one of the most important mindset shifts of your leadership journey: stop trying to become a better fundraiser and start becoming a Major Gift Leader. We'll explore why major gifts are the natural outcome of authentic leadership, how confidence is built through relationships rather than solicitation, and what it means to become the kind of leader major donors naturally want to invest in.

If you've ever felt uncomfortable asking for money, struggled to make fundraising a priority, or questioned whether you're the right person to lead your organization's fundraising efforts, this episode is for you. Your mission doesn't just need an Executive Director—it needs a Major Gift Leader. And becoming that leader may be the most important investment you ever make in your organization's future.

***NEW COHORT***

Introducing The Major Gift Leadership Cohort - exclusive 8-week coaching intensive for Executive Directors and nonprofit leaders who want to build authentic donor relationships that naturally lead to transformational gifts. Visit here to learn more: https://www.thefundcoach.com/cohort-waiting-list

FREE GUIDE: 5 Habits of Executive Directors Who Land Big Gifts: https://bit.ly/4hFkOth

Connect with me on LinkedIn: https://www.linkedin.com/in/mlduncan/

To get this video podcast in your inbox, visit and subscribe to The Weekly Huddle newsletter here: https://www.thefundcoach.com/opt-in

Let's Talk! Click here to schedule a Major Gift Strategy Session to get clarity on what your mission needs: https://www.thefundcoach.com/discovery-session-booking-page

Windfall - Wealth Analytics Report: https://analytics.windfall.com/partner/the-fund-coach

What if I told you that your next major donor may already be supporting your organization? Too many nonprofit leaders think major gifts begin with wealthy prospects they've never met. In reality, transformational gifts often come from donors who started with a modest, transactional gift and gradually developed a deeper relationship with the mission. The challenge isn't finding new donors—it's intentionally moving the donors you already have from transactional to relational to transformational. In this episode of Huddle Up with Mark The Fund Coach, I unpack what I call the Major Gift Trajectory and explain how donors naturally progress from making an initial gift to becoming passionate partners who make transformational investments. You'll learn why so many organizations get stuck treating donors like transactions, the relationship-building strategies that move donors forward, and how to create a system that consistently develops major gift opportunities. If you're ready to stop chasing one-time donations and start cultivating lifelong donor partnerships, this episode will give you a practical roadmap to help your supporters grow into your organization's most committed champions.

***NEW COHORT*** Introducing The Major Gift Leadership Cohort - exclusive 8-week coaching intensive for Executive Directors and nonprofit leaders who want to build authentic donor relationships that naturally lead to transformational gifts. Visit here to learn more: https://www.thefundcoach.com/cohort-waiting-list

FREE GUIDE: 5 Habits of Executive Directors Who Land Big Gifts: https://bit.ly/4hFkOth Connect with me on LinkedIn: https://www.linkedin.com/in/mlduncan/

To get this video podcast in your inbox, visit and subscribe here: https://www.thefundcoach.com/opt-in

Need Private Coaching? Click here to schedule a strategy session to discuss your fundraising needs: https://www.thefundcoach.com/discovery-session-booking-page

Windfall - Wealth Analytics Report: https://analytics.windfall.com/partner/the-fund-coach

Subscribe to the podcast on Apple - https://podcasts.apple.com/us/podcast/huddle-up-with-mark-the-fund-coach/id1799766114 or Spotify https://open.spotify.com/show/03LPM7zjoDMLV0OGPJBxTO?si=c730fc5b97a04854

Have you ever looked through your donor database and wondered what happened to some of your best supporters? They gave generously, attended your events, and seemed deeply connected to your mission. Then...they went quiet.

The good news is that silence doesn't necessarily mean they've lost interest. More often than not, they've simply fallen out of regular communication with your organization. In this episode of *Huddle Up with Mark The Fund Coach*, I share why major donors go quiet, the common mistakes nonprofit leaders make that unintentionally create distance, and simple, practical ways to reconnect before the relationship fades away.

If you're ready to stop chasing new donors and start strengthening relationships with the supporters who already believe in your mission, this episode is for you. Sometimes your next transformational gift doesn't come from finding a new donor—it comes from reconnecting with one who's been waiting to hear from you.

***NEW RESOURCE*** The Board Member's Guide to Fundraising (Without the Ask) - Check it Out: https://www.thefundcoach.com/the-board-member-s-guide-to-fundraising-without-the-ask

FREE GUIDE: 5 Habits of Executive Directors Who Land Big Gifts: https://bit.ly/4hFkOth Connect with me on LinkedIn: https://www.linkedin.com/in/mlduncan/

To get this video podcast in your inbox, visit and subscribe here: https://www.thefundcoach.com/opt-in

Need Private Coaching? Click here to schedule a strategy session to discuss your fundraising needs: https://www.thefundcoach.com/discovery-session-booking-page

Windfall - Wealth Analytics Report: https://analytics.windfall.com/partner/the-fund-coach

Subscribe to the podcast on Apple - https://podcasts.apple.com/us/podcast/huddle-up-with-mark-the-fund-coach/id1799766114 or Spotify https://open.spotify.com/show/03LPM7zjoDMLV0OGPJBxTO?si=c730fc5b97a04854

Most nonprofit leaders spend months—sometimes years—working to secure a major gift. But what happens after the donor says "yes"? Too often, organizations celebrate, send a thank-you letter, and move on to raising the next gift. That's a missed opportunity. In this episode of *Huddle Up with Mark The Fund Coach*, I'm talking about one of the biggest mistakes executive directors make after receiving a major gift and why stewardship is about so much more than gratitude. You'll learn how to turn a one-time donor into a lifelong partner by building trust, demonstrating impact, and creating meaningful relationships that lead to future transformational gifts. If you want to stop thinking of fundraising as a series of transactions and start building lasting partnerships with your donors, this episode is for you. Remember, the gift isn't the finish line—it's the beginning of an even greater opportunity to deepen the relationship and advance your mission.

***NEW RESOURCE*** The Board Member's Guide to Fundraising (Without the Ask) - Check it Out: https://www.thefundcoach.com/the-board-member-s-guide-to-fundraising-without-the-ask

FREE GUIDE: 5 Habits of Executive Directors Who Land Big Gifts: https://bit.ly/4hFkOth Connect with me on LinkedIn: https://www.linkedin.com/in/mlduncan/

To get this video podcast in your inbox, visit and subscribe here: https://www.thefundcoach.com/opt-in

Check out the Relationship Fundraising Academy: https://www.thefundcoach.com/rfa

Need 1:1 Coaching? Click here to schedule a strategy session to discuss your fundraising needs: https://www.thefundcoach.com/discovery-session-booking-page

Windfall - Wealth Analytics Report: https://analytics.windfall.com/partner/the-fund-coach

Subscribe to the podcast on Apple - https://podcasts.apple.com/us/podcast/huddle-up-with-mark-the-fund-coach/id1799766114 or Spotify https://open.spotify.com/show/03LPM7zjoDMLV0OGPJBxTO?si=c730fc5b97a04854

Are you unintentionally making your mission sound smaller than it really is? Many nonprofit leaders are passionate about their work, but when it comes to talking about their organization, they often focus on limitations instead of possibilities. They downplay the vision, minimize the impact, and hesitate to communicate the full potential of what their mission could achieve. In this episode of *Huddle Up with Mark The Fund Coach*, we're exploring why donors aren't inspired by small thinking—and why your ability to cast a compelling vision may be one of the most important fundraising skills you can develop. If you want to engage major donors, inspire greater generosity, and lead with confidence, it starts by helping others see what's possible. Starting a nonprofit is an exciting journey, but many founders quickly discover that passion alone isn't enough to sustain an organization. In this episode of Huddle Up with Mark The Fund Coach, Mark shares some of the most common fundraising and startup mistakes nonprofit leaders make—and how to avoid them. From researching whether your community truly needs another nonprofit to understanding that incorporation is only the beginning, you'll learn practical steps to build a stronger foundation for long-term success. Whether you're launching a new nonprofit or considering starting one, this episode will help you think strategically about fundraising, sustainability, and creating lasting impact.

***NEW RESOURCE*** The Board Member's Guide to Fundraising (Without the Ask) - Check it Out: https://www.thefundcoach.com/the-board-member-s-guide-to-fundraising-without-the-ask

FREE GUIDE: 5 Habits of Executive Directors Who Land Big Gifts: https://bit.ly/4hFkOth

Connect with me on LinkedIn: https://www.linkedin.com/in/mlduncan/

To get this video podcast in your inbox, visit and subscribe here: https://www.thefundcoach.com/opt-in

Check out the Relationship Fundraising Academy: https://www.thefundcoach.com/rfa

Need 1:1 Coaching? Click here to schedule a strategy session to discuss your fundraising needs: https://www.thefundcoach.com/discovery-session-booking-page

Windfall - Wealth Analytics Report: https://analytics.windfall.com/partner/the-fund-coach

Subscribe to the podcast on Apple - https://podcasts.apple.com/us/podcast/huddle-up-with-mark-the-fund-coach/id1799766114 or Spotify https://open.spotify.com/show/03LPM7zjoDMLV0OGPJBxTO?si=c730fc5b97a04854

Starting a nonprofit is an exciting journey, but many founders quickly discover that passion alone isn't enough to sustain an organization. In this episode of Huddle Up with Mark The Fund Coach, Mark shares some of the most common fundraising and startup mistakes nonprofit leaders make—and how to avoid them. From researching whether your community truly needs another nonprofit to understanding that incorporation is only the beginning, you'll learn practical steps to build a stronger foundation for long-term success. Whether you're launching a new nonprofit or considering starting one, this episode will help you think strategically about fundraising, sustainability, and creating lasting impact.

***NEW RESOURCE*** The Board Member's Guide to Fundraising (Without the Ask) - Check it Out: https://www.thefundcoach.com/the-board-member-s-guide-to-fundraising-without-the-ask

FREE GUIDE: 5 Habits of Executive Directors Who Land Big Gifts: https://bit.ly/4hFkOth

Connect with me on LinkedIn: https://www.linkedin.com/in/mlduncan/ To get this video podcast in your inbox, visit and subscribe here: https://www.thefundcoach.com/opt-in

Check out the Relationship Fundraising Academy: https://www.thefundcoach.com/rfa

Need 1:1 Coaching? Click here to schedule a strategy session to discuss your fundraising needs: https://www.thefundcoach.com/discovery-session-booking-page

Windfall - Wealth Analytics Report: https://analytics.windfall.com/partner/the-fund-coach

Subscribe to the podcast on Apple - https://podcasts.apple.com/us/podcast/huddle-up-with-mark-the-fund-coach/id1799766114 or

Spotify https://open.spotify.com/show/03LPM7zjoDMLV0OGPJBxTO?si=c730fc5b97a04854

What if one of the biggest limitations on your organization's fundraising success is the belief that major gifts are only for campaigns? Too many nonprofits wait until they're launching a capital campaign or special initiative before they begin engaging major donors. The problem is that meaningful donor relationships can't be rushed when a funding need arises. In this episode of Huddle Up with Mark The Fund Coach, we're exploring why major gifts should be a year-round fundraising strategy, not a campaign tactic. You'll learn how organizations unintentionally limit donor engagement when they only pursue major gifts during campaigns, and why building consistent relationships with major donors can lead to stronger fundraising, greater sustainability, and transformational support for your mission. Let's Huddle Up!

FREE GUIDE: 5 Habits of Executive Directors Who Land Big Gifts: https://bit.ly/4hFkOth

Connect with me on LinkedIn: https://www.linkedin.com/in/mlduncan/ To get this video podcast in your inbox, visit and subscribe here: https://www.thefundcoach.com/opt-in

Check out the Relationship Fundraising Academy: https://www.thefundcoach.com/rfa

Need Private Coaching? Click here to schedule a strategy session to discuss your fundraising needs: https://www.thefundcoach.com/discovery-session-booking-page

Windfall - Wealth Analytics Report: https://analytics.windfall.com/partner/the-fund-coach

What happens when the executive director and the board stop operating separately—and start partnering together around fundraising? In this episode of Huddle Up with Mark The Fund Coach, we explore how healthy fundraising cultures are built through strong relationships, shared ownership, and intentional collaboration between nonprofit leaders and their boards. Too often, fundraising becomes the burden of one person while board members remain unsure of their role. But when boards understand how to engage relationally—without pressure to make the ask—everything changes. This conversation will help nonprofit leaders rethink board engagement and discover how stronger partnerships can lead to deeper donor trust, greater impact, and more sustainable fundraising success.

FREE GUIDE: 5 Habits of Executive Directors Who Land Big Gifts: https://bit.ly/4hFkOth

Connect with me on LinkedIn: https://www.linkedin.com/in/mlduncan/

To get this video podcast in your inbox, visit and subscribe here: https://www.thefundcoach.com/opt-in

Check out the Relationship Fundraising Academy: https://www.thefundcoach.com/rfa

Need 1:1 Coaching? Click here to schedule a strategy session to discuss your fundraising needs: https://www.thefundcoach.com/discovery-session-booking-page

Windfall - Wealth Analytics Report: https://analytics.windfall.com/partner/the-fund-coach

One of the biggest reasons nonprofit leaders struggle to secure transformational gifts has nothing to do with donor wealth — it has everything to do with the confidence behind the ask. In this episode of Huddle Up with Mark The Fund Coach, Mark dives into why leaders often ask too small, how fear and scarcity thinking quietly limit fundraising success, and why your ask communicates how much you truly value your mission. If you’ve ever hesitated before making a major gift ask or wondered why wealthy donors aren’t stepping up at higher levels, this episode will challenge the way you think about fundraising leadership, donor psychology, and the power of confident vision. Because major donors don’t just invest in causes — they invest in conviction.

FREE GUIDE: 5 Habits of Executive Directors Who Land Big Gifts: https://bit.ly/4hFkOth

Connect with me on LinkedIn: https://www.linkedin.com/in/mlduncan/

To get this video podcast in your inbox, visit and subscribe here: https://www.thefundcoach.com/opt-in

Check out the Relationship Fundraising Academy: https://www.thefundcoach.com/rfa

Need 1:1 Coaching? Click here to schedule a strategy session to discuss your fundraising needs: https://www.thefundcoach.com/discovery-session-booking-page

Windfall - Wealth Analytics Report: https://analytics.windfall.com/partner/the-fund-coach

Subscribe to the podcast on Apple -https://podcasts.apple.com/us/podcast/huddle-up-with-mark-the-fund-coach/id1799766114 or Spotify https://open.spotify.com/show/03LPM7zjoDMLV0OGPJBxTO?si=c730fc5b97a04854

In this episode of Huddle Up with Mark The Fund Coach, I break down how to run a fundraising event that does more than sell tickets—it creates real major gift opportunities. We talk about securing sponsorships to cover event costs, setting a clear net fundraising goal, and most importantly, building meaningful connections with attendees that lead to transformational follow-up conversations. If you want your next event to strengthen donor relationships and grow major gifts instead of just creating another transactional experience, this episode is for you. Let's Huddle Up!