Whenever my grandfather was asked what I did for a living, he’d grin and say, “Oh, she’s a professional beggar – and very good at it.”

He meant it playfully. But that joke pointed to something deeper: how fundraising is often viewed in American culture – and sometimes, how we as fundraisers view ourselves.

This work can feel loaded. Talking about money brings up all kinds of things: values, power, pride, fear of rejection. It’s personal. And when that discomfort goes unchecked, it sneaks into our conversations and undermines our confidence.

But here’s what I’ve learned: Your mindset matters more than your pitch.

How you feel about money shapes how you talk about it. And that directly affects whether you avoid the big asks – or step into them with clarity and purpose.

Over the years, I’ve noticed three mindset shifts that help fundraisers move past the awkwardness and into authentic, effective conversations. I call them the 3 Rs: Reciprocity, Receivership, and Reframing.
​
Let’s walk through them.

One of the most harmful myths in fundraising is the idea that we’re taking something from people. That donors are losing when they say yes.

That’s not what’s happening.

Giving is about alignment. When a donor gives, they’re not being depleted – they’re investing in meaning. They’re making their values visible. They’re stepping into a story that’s bigger than themselves.

That’s not taking. That’s inviting them in.

I’ve watched donors light up – not because of tote bags or nameplates – but because they felt connected. When we approach conversations with the understanding that there’s value on both sides, it changes how we show up.

Try this: When a donor shares why they give, listen closely. Then reflect it back. Say, “It means a lot to me that this work aligns with your values.” That simple moment of recognition reinforces that this is a relationship – not a transaction.

Let me ask you something: when someone picks up the lunch tab, do you fidget? When they compliment your work, do you wave it off or make a joke?

That matters more than you think.

If you struggle to receive in small, everyday moments, it’s going to be tough to stand still and grounded when it’s time to receive something much bigger – like a major gift.

Fundraising isn’t just about facilitating generosity. It’s about receiving it. That means knowing your own worth, your organization’s worth, and the worth of the mission you represent.

You’re not just asking for money. You’re offering someone the chance to invest in something meaningful.
​
Try this: The next time someone compliments you – on your work, your outfit, your presentation – just say, “Thank you.” No hedging. No “Oh, this old thing.” Practicing that kind of presence builds your capacity to receive with grace and confidence.

I’ve worked with some truly talented fundraisers – smart, strategic, big-picture thinkers – who freeze at the edge of the ask. I’ve done it myself from time to time.

The relationship is there. The timing is right. The groundwork has been laid. But when it’s time to actually say the number... they stall out.

There’s an old joke in our field about someone like that:
“How is <<that fundraiser>> like a 7/11 store?”
“They never close.”

Funny – but also kind of painful. Because many of us have been that person. I know I have.

We hesitate because we don’t want to feel pushy. We worry we’ll mess up the relationship. But here’s the truth: donors – especially high-net-worth donors – know what we do. They expect us to ask.

And when we don’t? It doesn’t protect the relationship. It creates confusion. When trust has been built, the ask isn’t a surprise. It’s the next logical step.

​Try this: Start using this phrase in conversations: “I’d love to talk with you about a way to deepen your impact.” It’s warm. It’s clear. And it helps you move into the ask without making it weird.

So, what does this mean for you?

If you want to grow as a fundraiser, start by checking your mindset.

• Do you believe there’s value on both sides of the conversation?
• Are you willing to receive, not just facilitate?
• Can you honor the relationship by being direct about the opportunity?

Fundraising isn’t begging. And it’s not manipulation.

It’s invitation. It’s partnership. It’s a shared pursuit of something that matters.

My grandfather may have called me a “professional beggar” – but he wasn’t wrong about the skill it takes to do this work well. He just didn’t know the half of it.

Get your 3 Rs in alignment, and you’ll stop feeling like you’re asking for a favor – and start showing up like the professional you already are.

Cheers!

​Jessica

P.S. Like this kind of insight? Subscribe to Real Deal Fundraising and get my best articles, tools, and curated resources every week – including webinars, videos, and free downloads.

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 Back in 2007, I was prepping for a presentation to my peers – young professionals like me, running fundraising call centers across the country. We were mostly in our 20s, ambitious, a little scrappy, and working in a company culture that leaned casual.

I was thinking about wearing a skirt suit. It felt like the right thing for the moment. But I was second-guessing it hard.

What if they thought I was stuck up? Or trying too hard? Or trying to be something I wasn’t?

I asked my husband what he thought.

He said, “Wear the suit.”

I explained the whole situation again, sure he didn’t get it.

He said again, “Wear. The. Suit.”

By the third time, I was exasperated.

That’s when he clarified: “If you’re going to wear the suit, wear the suit... Stand in it. Own it. Don’t apologize for it. You’re stepping into the authority you already have – but you’ve got to embody it. If you do that, what anyone else thinks won’t matter.”

That moment stuck.

​Because it was never about the suit. It was about how I carried myself in the suit.

You can’t control how other people read you. But you can decide how you show up.

You can choose to walk into the room with the posture, presence, and clarity of someone who belongs there. You can lead – even when you're still growing.

So whatever your “suit” is – your outfit, your opening line, your tone – don’t just put it on.

Wear it.

Let’s bring it into your world:
What’s your version of “the suit”? That thing that helps you stand taller and lead stronger when it counts?

Drop it in the comments – I’d love to hear what helps you show up with presence.

Cheers!

​Jessica

P.S. Like this kind of insight? Subscribe to Real Deal Fundraising and get my best articles, tools, and curated resources every week – including webinars, videos, and free downloads.

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I used to think donor interviews for our legacy giving newsletter were just good stewardship – a warm thank-you to generous folks who’d already made a planned gift.

Back then, part of my “gal Friday” role at the university was to call these donors, hear their stories, and write up little features for our newsletter. It felt like we were shining a light on their kindness and leaving it at that.

Then something surprising happened. After a few issues, my inbox started filling with messages:

• “How do I make a bequest?”
• “Can you send me sample language?”
• “I think I want to do this too.”

That’s when I realized: peer stories are one of the most powerful planned giving lead generators you’ll ever have.

Planned giving can feel awkward to talk about – it’s wrapped up in big questions about life, death, and legacy. But when donors see someone just like them, sharing why they chose to leave a gift, it shifts the conversation. Suddenly it’s not about confronting mortality – it’s about hope for the future.

And when those leads came in, the follow-up conversations weren’t awkward at all. I wasn’t “convincing” anyone; I was simply giving them the tools they’d already decided they wanted.

If you have even one donor who’s named your organization in their will, you have a powerful story to tell. And those stories can spark more conversations – and more commitments – than any brochure or website copy ever could.
​
Here are five simple, effective ways to start generating planned giving leads right now, starting with the most important one…

Start with real people who’ve already made a legacy commitment. Interview them, ask thoughtful questions, and tell their story with heart. These five questions help bring their motivations to life:

• What motivated you to include [Your Organization] in your estate?
• What does this gift mean to you?
• How did you become committed to the work of [Your Organization]?
• What would you say to others considering a gift like this?
• What is your dearest hope for the future of [Your Organization]?

Share those stories in newsletters, emails, social media, and video. These stories are your campaign – they create connection, trust, and curiosity.

You need a place to send people who want more info – don’t make them hunt for it. This doesn’t have to be complicated. Just make sure it includes:

• Sample bequest language
• A downloadable letter of intent
• A list of beneficiary options (retirement accounts, IRAs, life insurance, etc.)
• A contact form or a real name and email for follow-up

This is your annual window to talk openly about legacy giving – especially with donor stories. Tie them to helpful content like estate planning tips, FAQs, or “3 Easy Ways to Leave a Legacy” guides. Light, approachable, and packed with value.

Don’t let October do all the heavy lifting. Bring it back around with a spring campaign using your existing content – maybe add a new testimonial, or reframe the messaging. Familiarity builds comfort.

Flip that reply device over and include a quick checkbox survey:
☑ I’ve already included [Org Name] in my estate plans
☑ I’d like more information
☑ Please send me sample bequest language

This low-lift tweak has sparked real results for many nonprofits – and costs zero extra to implement.

If your nonprofit does just these five things, you’ll be light years ahead of most organizations in planned giving marketing. And the best part? None of them require new dollars in the budget.
​
That’s a win for your donors – and a big step toward your organization’s long-term financial stability.

Planned giving is one of the most powerful ways to future-proof your mission – and October is the perfect time to talk about it. This digital bundle is packed with tools to help you celebrate, educate, and inspire your supporters to leave a lasting legacy.

Here’s what’s inside:

1. ✍️ Planned Gift Landing Page Web Copy – $15.99 value
   Pre-written, customizable copy to get your new page up and running fast.
2. ✍️ Planned Gift Letter of Intent – $15.99 value
   A ready-to-go Canva template that makes it easy for donors to document their intentions.
3. 📜 Sample Bequest Language – $15.99 value
   Plug-and-play language your donors can use in their wills.
4. 📅 Digital Marketing Plan for National Estate Planning Awareness Week – $34.99 value
   Your entire week planned out with posting schedules, content ideas, and engagement tips.
5. 📲 Social Media Planned Giving Templates (10) – $24.99 value
   Customizable, scroll-stopping designs for Facebook, Instagram, and X.
6. 🎁 Bonus: Email Headers for Promoting Planned Giving (3) – FREE
   Designed to pair with your planned giving email blasts.

​💡 Total value: $114.95  –  You pay just $84.99. That’s 26% off.

And here’s the kicker:

• Planned giving brings an average return of $56.83 for every $1 spent.
• It often boosts annual giving, not just future gifts.
• And it opens the door to new, deeply loyal donors.

📥 Once you purchase, you’ll receive a downloadable PDF with links, setup instructions, and a tutorial video to walk you through the whole process.

👩‍💼 Made by me – Jessica Neno Cloud, CFRE – with 20+ years in the field helping fundraisers like you take real, doable steps toward long-term success.

👉 Ready to roll? Get your bundle now and make this October count.

Cheers!

If you liked this…

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• How to Talk About Death and Taxes: Getting Comfortable Having Planned Giving Conversations

Starting a nonprofit can feel like launching a rocket with duct tape and a dream. You’ve got passion, vision, and maybe a few donors – but not nearly enough resources. So when someone offers to help with fundraising in exchange for a cut of the money raised, it might feel like a godsend.

It’s not.

(Sorry, I didn’t do that justice. Let me try again.)

IT’S NOTTTTTT!!!!

Commission-based fundraising is one of the first ethical missteps many new nonprofits make – and not because they’re careless. It’s because they don’t know any better. Meanwhile, there are companies that do know better – and they prey on organizations still trying to find their footing.
​
Let’s talk about why commission-based fundraising is a problem, the myths that keep it going, and what to do instead.

Commission-based pay structures – where fundraisers receive a percentage of what they raise – are widely considered unethical in the nonprofit sector.

Not because it’s illegal. It’s not. The IRS doesn’t prohibit it. But that’s not the bar you want to be setting for your organization.

Professional groups like the Association of Fundraising Professionals (AFP) have long held that this practice crosses ethical lines. Here’s why:

• It creates a conflict of interest. Tying compensation to gift size can push fundraisers to pressure donors or overpromise – damaging trust along the way.
• It hurts donor relationships. If a donor thinks your gift officer’s paycheck depends on their generosity, that can leave a bad taste and end future giving.
• It turns fundraising into a transaction. This work is about partnership, not procurement. Your mission isn’t for sale.

I see this come up all the time in social media groups for nonprofit founders. At least once a month, someone will ask, “Is commission-based fundraising okay?” They’re just trying to figure out how to move forward with no staff and limited funds.

And every time, like clockwork, commission-based fundraising companies show up in the comments to say, “It’s totally fine!” and there I am, in the replies, trying to explain why it’s not fine.
​
I’m not trying to be the fun police. I’ve just seen how this plays out – and it’s never pretty. New nonprofits deserve better than shortcuts that backfire.

Let’s tackle some of the most common counterpoints I hear – because these arguments pop up over and over again:

💬 “Isn’t salary technically paid from money raised? So what’s the difference?”
Yes, most nonprofit salaries come from donated funds. The difference is in structure. A salary pays for a fundraiser’s time, experience, and judgment. It’s not tied to the outcome of a specific gift. That distinction matters – because it keeps the motivation focused on relationships, not revenue.

💬 “There’s no law against it, so it must be fine.”
Ethics and legality aren’t the same thing. Just because something’s allowed doesn’t make it wise – or aligned with best practices. Commission-based fundraising can hurt your credibility with savvy donors who know the difference.
​
💬 “We can’t afford a salary. Commission is all we can offer.”
This is the one that really pulls at the heart. I get it. But commission isn’t your only option. If you don’t have funds to hire someone, try this instead:

• Lean on your board. A strong fundraising board isn’t just for show. These folks should give and help you find new supporters.
• Recruit mission-aligned volunteers. People who believe in your work and have strong networks can be powerful early advocates.
• Learn the craft yourself. Fundraising is about building trust. You don’t need to know everything today – you just need to start showing up.

Outsourcing might sound like a great fix, especially when you’re wearing every hat. And there are reputable consultants who can teach and guide. But outsourcing your entire fundraising operation – especially donor relationships – is risky business.

Here’s what you give up when you hand it all off:

• Authentic connection. Donors give to people, not platforms. If someone else is forming the relationship, they’re the one who earns the trust.
• Control of your message. You need to know what your donors are hearing and how they’re being treated.
• Your own learning curve. Early fundraising is messy. But that mess teaches you what works – and what doesn’t. You don’t want to miss those lessons.

​
Fundraising isn’t something to delegate away. It’s a core part of your leadership role.

If you’re building a nonprofit from scratch, start here:

✅ Build a fundraising board.
Don’t settle for warm bodies. Find people who will give, ask, and connect you with others who care.

✅ Invest your time in relationships.
Whether someone gives $10 or $10,000, treat them like a partner in your mission. Show up. Say thank you. Follow up. Every relationship counts.

✅ Start small and grow with purpose.
You don’t need a six-figure campaign to begin. Start where you are, stay consistent, and build momentum step by step.
​
✅ Find a mentor – not a miracle.
Look for people who will teach you, not sell you. A good advisor will build your capacity – not just close deals.

Commission-based fundraising isn’t just an ethics issue – it’s a growth issue. It can derail donor trust, distract you from mission work, and create headaches you don’t need.

Starting a nonprofit is brave work. And it takes guts to say no to the fast and easy path when you’re feeling the pressure to raise money quickly.

But there is a way to fundraise with integrity. It starts with doing the work yourself, building trust one conversation at a time, and keeping your eyes on the long game.

You don’t have to build your mission alone.

But you do have to build it right.

And you will.
​
Cheers!

P.S. Like this kind of insight?
Subscribe to Real Deal Fundraising and get my best articles, tools, and curated resources every week – including webinars, videos, and free downloads.

If you liked this… 

• Why Nonprofits Can’t Afford to Sleep on IRA Rollovers
• Cut Through the Clutter: Focus on the Two Planned Giving Options That Really Work
• Your Board Wants to Help with Fundraising – They Just Don’t Know How
• How to Build a Philanthropy Calendar That Drives Digital Donations
• Spring Cleaning for Fundraisers: Organizing Planned Giving Documentation

IRA rollovers are the best of both worlds. They let donors give from their assets, not their income – so these gifts are often larger than what someone could give from their checkbook. And here’s the best part: the funds can be put to use immediately by the nonprofit.

Still, many fundraisers hesitate to talk about Qualified Charitable Distributions (QCDs) – also known as IRA rollover gifts – because they don’t feel confident answering donor questions. But here’s the truth: donors rarely ask complicated questions. They just want to understand the basics.

If we want to receive these powerful gifts, we need to be ready with clear, simple answers.
​
Here are the top three questions I hear most often – plus how to respond in a way that builds trust and inspires action.

In 2025, the annual QCD limit is $108,000 per individual, indexed for inflation. If both spouses have IRAs, a household can give up to $216,000 in a single year.
​
Keep in mind: this is the total giving limit per IRA account per tax year. So if you've already made other QCDs this year, you’ll want to keep a tally toward that annual cap.

If you’re not already promoting IRA rollovers, this is the time to start. And no – you don’t have to start from scratch.

​✅ Grab the IRA Rollover Promotion Bundle – Everything You Need to Promote QCDs

This $99 bundle includes:

• 🖥️ Web language to launch your IRA Rollover landing page
• 📽️ Three video scripts to educate and inspire donors
• 📱 Nine social media templates for Facebook, Instagram, and Twitter
• 💌 Three plug-and-play email templates for key seasons
• 🖋️ A 12-slide presentation deck for board meetings, webinars, or donor events

You’ll get a downloadable PDF with links to every template, setup instructions, and a short tutorial video. Created by me – Jessica Neno Cloud, CFRE – after 20+ years in fundraising, this bundle is built to help you raise more, with less stress and guesswork.

​From 2019 to 2021, giving through IRAs jumped 390%. This isn’t a trend – it’s a tidal wave. Let’s make sure your nonprofit is riding it.

Want a free way to get started?

Download my free resource, Calendar of IRA Rollover Promotions – a simple tool to help you map out smart, strategic outreach across the calendar year.
​
👉 Download the Free Calendar

Cheers!

P.S. Like this kind of insight?

Subscribe to Real Deal Fundraising and get my best articles, tools, and curated resources every week – including webinars, videos, and free downloads.

IRA Rollover References Resources

• Qualified charitable distributions allow eligible IRA owners up to $100,000 in tax-free gifts to charity (IRS)
• What is a qualified charitable distribution? (Fidelity)
• New reporting requirement for Qualified Charitable Distributions (Wolters Kluwer)

If you liked this…

• Why Nonprofits Can’t Afford to Sleep on IRA Rollovers
• Cut Through the Clutter: Focus on the Two Planned Giving Options That Really Work
• Your Board Wants to Help with Fundraising – They Just Don’t Know How
• How to Build a Philanthropy Calendar That Drives Digital Donations
• Spring Cleaning for Fundraisers: Organizing Planned Giving Documentation