Jessica Cloud, CFRE | Real Deal Fundraising
@jcloudrealdeal.bsky.social
Tips to help nonprofits raise ⬆️ 💵
https://linktr.ee/jcloudrealdeal
https://linktr.ee/jcloudrealdeal
A missed field. A skipped exclusion. A donor left off an invite.
Data mistakes don’t just waste time – they can cost you real gifts.
If you’re tired of scrambling after the fact, it’s time to get ahead of the problem.
Data mistakes don’t just waste time – they can cost you real gifts.
If you’re tired of scrambling after the fact, it’s time to get ahead of the problem.
November 14, 2025 at 5:15 PM
A missed field. A skipped exclusion. A donor left off an invite.
Data mistakes don’t just waste time – they can cost you real gifts.
If you’re tired of scrambling after the fact, it’s time to get ahead of the problem.
Data mistakes don’t just waste time – they can cost you real gifts.
If you’re tired of scrambling after the fact, it’s time to get ahead of the problem.
You know that sinking feeling when a data file comes back… wrong?
You asked for lapsed donors.
They pulled anyone who didn’t give last month.
Now you're days behind – and your mailing window’s shrinking.
Most fundraisers were never taught how to ask for data the right way. That’s not your fault.
You asked for lapsed donors.
They pulled anyone who didn’t give last month.
Now you're days behind – and your mailing window’s shrinking.
Most fundraisers were never taught how to ask for data the right way. That’s not your fault.
November 12, 2025 at 6:03 PM
You know that sinking feeling when a data file comes back… wrong?
You asked for lapsed donors.
They pulled anyone who didn’t give last month.
Now you're days behind – and your mailing window’s shrinking.
Most fundraisers were never taught how to ask for data the right way. That’s not your fault.
You asked for lapsed donors.
They pulled anyone who didn’t give last month.
Now you're days behind – and your mailing window’s shrinking.
Most fundraisers were never taught how to ask for data the right way. That’s not your fault.
If you're a fundraiser who relies on data (that’s all of us), here's one way to instantly improve your outcomes:
Write better data requests.
Take five minutes now to:
✅ Avoid five days of email ping-pong
✅ Protect your deadlines
✅ Build trust with your CRM team
✅ Stop scrambling
Write better data requests.
Take five minutes now to:
✅ Avoid five days of email ping-pong
✅ Protect your deadlines
✅ Build trust with your CRM team
✅ Stop scrambling
November 10, 2025 at 8:28 PM
If you're a fundraiser who relies on data (that’s all of us), here's one way to instantly improve your outcomes:
Write better data requests.
Take five minutes now to:
✅ Avoid five days of email ping-pong
✅ Protect your deadlines
✅ Build trust with your CRM team
✅ Stop scrambling
Write better data requests.
Take five minutes now to:
✅ Avoid five days of email ping-pong
✅ Protect your deadlines
✅ Build trust with your CRM team
✅ Stop scrambling
📣 Small shop fundraisers: Want a Giving Tuesday tip that actually saves you time?
Pre-load your pledge list.
Ask board members and loyal donors for early commitments in October. Then, on Giving Tuesday, all you’re doing is following up.
Pre-load your pledge list.
Ask board members and loyal donors for early commitments in October. Then, on Giving Tuesday, all you’re doing is following up.
October 24, 2025 at 5:45 PM
📣 Small shop fundraisers: Want a Giving Tuesday tip that actually saves you time?
Pre-load your pledge list.
Ask board members and loyal donors for early commitments in October. Then, on Giving Tuesday, all you’re doing is following up.
Pre-load your pledge list.
Ask board members and loyal donors for early commitments in October. Then, on Giving Tuesday, all you’re doing is following up.
💡Want to get your major donors more involved in Giving Tuesday?
Don’t wait until the week before to ask for a gift.
Invite them in early – as collaborators, not just check writers.
Don’t wait until the week before to ask for a gift.
Invite them in early – as collaborators, not just check writers.
October 22, 2025 at 5:15 PM
💡Want to get your major donors more involved in Giving Tuesday?
Don’t wait until the week before to ask for a gift.
Invite them in early – as collaborators, not just check writers.
Don’t wait until the week before to ask for a gift.
Invite them in early – as collaborators, not just check writers.
📅 Giving Tuesday isn’t a one-day campaign. It’s your launchpad.
When you treat it like a one-time push, you miss the real potential: momentum.
This is the moment your donors start paying attention again.
When you treat it like a one-time push, you miss the real potential: momentum.
This is the moment your donors start paying attention again.
October 20, 2025 at 7:06 PM
📅 Giving Tuesday isn’t a one-day campaign. It’s your launchpad.
When you treat it like a one-time push, you miss the real potential: momentum.
This is the moment your donors start paying attention again.
When you treat it like a one-time push, you miss the real potential: momentum.
This is the moment your donors start paying attention again.
“Why do you need my gift if you just got that big one from [insert donor]?”
That question hurts.
Not because it’s mean.
Because it’s valid.
And if we dodge it, we lose trust.
#fundraising #npsky
That question hurts.
Not because it’s mean.
Because it’s valid.
And if we dodge it, we lose trust.
#fundraising #npsky
October 17, 2025 at 3:31 PM
“Why do you need my gift if you just got that big one from [insert donor]?”
That question hurts.
Not because it’s mean.
Because it’s valid.
And if we dodge it, we lose trust.
#fundraising #npsky
That question hurts.
Not because it’s mean.
Because it’s valid.
And if we dodge it, we lose trust.
#fundraising #npsky
🚨 Donor throws a curveball.
Your brain stalls.
You think:
“What do I even say to that?”
If you’ve worked in fundraising for any length of time, you know the feeling.
That one question that’s a little awkward. A little skeptical. Maybe even a little aggressive.
#fundraising #npsky
Your brain stalls.
You think:
“What do I even say to that?”
If you’ve worked in fundraising for any length of time, you know the feeling.
That one question that’s a little awkward. A little skeptical. Maybe even a little aggressive.
#fundraising #npsky
October 15, 2025 at 4:45 PM
🚨 Donor throws a curveball.
Your brain stalls.
You think:
“What do I even say to that?”
If you’ve worked in fundraising for any length of time, you know the feeling.
That one question that’s a little awkward. A little skeptical. Maybe even a little aggressive.
#fundraising #npsky
Your brain stalls.
You think:
“What do I even say to that?”
If you’ve worked in fundraising for any length of time, you know the feeling.
That one question that’s a little awkward. A little skeptical. Maybe even a little aggressive.
#fundraising #npsky
When a donor asks something tough, here’s my go-to:
Listen. Acknowledge. Support. Continue.
It’s not a script.
It’s not about smoothing things over.
It’s how you move through the hard stuff without losing the relationship.
#fundraising #npsky
Listen. Acknowledge. Support. Continue.
It’s not a script.
It’s not about smoothing things over.
It’s how you move through the hard stuff without losing the relationship.
#fundraising #npsky
October 13, 2025 at 11:07 PM
When a donor asks something tough, here’s my go-to:
Listen. Acknowledge. Support. Continue.
It’s not a script.
It’s not about smoothing things over.
It’s how you move through the hard stuff without losing the relationship.
#fundraising #npsky
Listen. Acknowledge. Support. Continue.
It’s not a script.
It’s not about smoothing things over.
It’s how you move through the hard stuff without losing the relationship.
#fundraising #npsky
“Hang in there.”
“We’ll get you an admin soon.”
“It’s just a busy season.”
You’ve heard it.
So have I.
And deep down, we all know what it really means:
You're going to do the job of three people, with one salary, and no support.
“We’ll get you an admin soon.”
“It’s just a busy season.”
You’ve heard it.
So have I.
And deep down, we all know what it really means:
You're going to do the job of three people, with one salary, and no support.
October 10, 2025 at 5:15 PM
“Hang in there.”
“We’ll get you an admin soon.”
“It’s just a busy season.”
You’ve heard it.
So have I.
And deep down, we all know what it really means:
You're going to do the job of three people, with one salary, and no support.
“We’ll get you an admin soon.”
“It’s just a busy season.”
You’ve heard it.
So have I.
And deep down, we all know what it really means:
You're going to do the job of three people, with one salary, and no support.
You ever see a meme and think, “Oof. That’s too real”?
I shared one on TikTok and the responses from my fellow fundraisers were funny.
People laughed. Hard.
But under the humor?
There was something else.
Exhaustion.
Resignation.
The quiet ache of doing too much for too long.
I shared one on TikTok and the responses from my fellow fundraisers were funny.
People laughed. Hard.
But under the humor?
There was something else.
Exhaustion.
Resignation.
The quiet ache of doing too much for too long.
October 8, 2025 at 4:31 PM
You ever see a meme and think, “Oof. That’s too real”?
I shared one on TikTok and the responses from my fellow fundraisers were funny.
People laughed. Hard.
But under the humor?
There was something else.
Exhaustion.
Resignation.
The quiet ache of doing too much for too long.
I shared one on TikTok and the responses from my fellow fundraisers were funny.
People laughed. Hard.
But under the humor?
There was something else.
Exhaustion.
Resignation.
The quiet ache of doing too much for too long.
Recently, I turned a TikTok meme into a nonprofit fundraiser reality check.
I said, “Let’s pretend the comment section is the search history of a burnout nonprofit fundraiser”:
I said, “Let’s pretend the comment section is the search history of a burnout nonprofit fundraiser”:
October 7, 2025 at 2:45 AM
Recently, I turned a TikTok meme into a nonprofit fundraiser reality check.
I said, “Let’s pretend the comment section is the search history of a burnout nonprofit fundraiser”:
I said, “Let’s pretend the comment section is the search history of a burnout nonprofit fundraiser”:
Donors don’t want more noise.
They want connection.
That’s why analog is making a quiet comeback in #fundraising.
Mail’s getting opened.
Phones are getting answered.
This isn’t ditching digital – just rebalancing.
Reply “Send it” for the full post.
#npsky
They want connection.
That’s why analog is making a quiet comeback in #fundraising.
Mail’s getting opened.
Phones are getting answered.
This isn’t ditching digital – just rebalancing.
Reply “Send it” for the full post.
#npsky
October 3, 2025 at 6:03 PM
Donors don’t want more noise.
They want connection.
That’s why analog is making a quiet comeback in #fundraising.
Mail’s getting opened.
Phones are getting answered.
This isn’t ditching digital – just rebalancing.
Reply “Send it” for the full post.
#npsky
They want connection.
That’s why analog is making a quiet comeback in #fundraising.
Mail’s getting opened.
Phones are getting answered.
This isn’t ditching digital – just rebalancing.
Reply “Send it” for the full post.
#npsky
Fundraising’s next edge isn’t in your subject line.
It’s in the mailbox.
On the phone.
With a real human voice.
The digital pile-up is real.
Analog isn’t nostalgic.
It’s profitable.
Reply “Real” for my full take.
#fundraising #npsky
It’s in the mailbox.
On the phone.
With a real human voice.
The digital pile-up is real.
Analog isn’t nostalgic.
It’s profitable.
Reply “Real” for my full take.
#fundraising #npsky
October 1, 2025 at 5:15 PM
Fundraising’s next edge isn’t in your subject line.
It’s in the mailbox.
On the phone.
With a real human voice.
The digital pile-up is real.
Analog isn’t nostalgic.
It’s profitable.
Reply “Real” for my full take.
#fundraising #npsky
It’s in the mailbox.
On the phone.
With a real human voice.
The digital pile-up is real.
Analog isn’t nostalgic.
It’s profitable.
Reply “Real” for my full take.
#fundraising #npsky
We handwrote 200 postcards last year.
Messy & real and Giving Tuesday crushed it.
Same with phones: helped a phonathon go from $134K to $396K.
Young alumni? 17% participation.
Analog isn’t dead. It works.
Reply “Postcard” for the full article.
#npsky #fundraising
Messy & real and Giving Tuesday crushed it.
Same with phones: helped a phonathon go from $134K to $396K.
Young alumni? 17% participation.
Analog isn’t dead. It works.
Reply “Postcard” for the full article.
#npsky #fundraising
September 29, 2025 at 9:15 PM
We handwrote 200 postcards last year.
Messy & real and Giving Tuesday crushed it.
Same with phones: helped a phonathon go from $134K to $396K.
Young alumni? 17% participation.
Analog isn’t dead. It works.
Reply “Postcard” for the full article.
#npsky #fundraising
Messy & real and Giving Tuesday crushed it.
Same with phones: helped a phonathon go from $134K to $396K.
Young alumni? 17% participation.
Analog isn’t dead. It works.
Reply “Postcard” for the full article.
#npsky #fundraising
There’s a kind of presence that doesn’t come from being flashy or polished.
It comes from being calm. Certain. Clear.
In fundraising, that’s what gravitas really is.
It comes from being calm. Certain. Clear.
In fundraising, that’s what gravitas really is.
September 26, 2025 at 4:15 PM
There’s a kind of presence that doesn’t come from being flashy or polished.
It comes from being calm. Certain. Clear.
In fundraising, that’s what gravitas really is.
It comes from being calm. Certain. Clear.
In fundraising, that’s what gravitas really is.
Most fundraisers obsess over the words.
The story. The pitch. The ask.
But here’s what I learned from an executive presence coach:
The story. The pitch. The ask.
But here’s what I learned from an executive presence coach:
September 24, 2025 at 4:09 PM
Most fundraisers obsess over the words.
The story. The pitch. The ask.
But here’s what I learned from an executive presence coach:
The story. The pitch. The ask.
But here’s what I learned from an executive presence coach:
Walked into a networking event in fishnets and suede boots – feeling confident, but wondering:
“Can a woman really move up in leadership dressed like this?”
“Can a woman really move up in leadership dressed like this?”
September 22, 2025 at 3:05 PM
Walked into a networking event in fishnets and suede boots – feeling confident, but wondering:
“Can a woman really move up in leadership dressed like this?”
“Can a woman really move up in leadership dressed like this?”
You don’t need a new template.
You need a new lens.
Stop writing what would convince you.
Start writing for how they decide.
Feel. Path. Ask. Why.
Hit all four – and you’re persuading, not just writing.
DM me if you want to build smarter appeals.
#fundraising #npsky
You need a new lens.
Stop writing what would convince you.
Start writing for how they decide.
Feel. Path. Ask. Why.
Hit all four – and you’re persuading, not just writing.
DM me if you want to build smarter appeals.
#fundraising #npsky
September 19, 2025 at 5:15 PM
You don’t need a new template.
You need a new lens.
Stop writing what would convince you.
Start writing for how they decide.
Feel. Path. Ask. Why.
Hit all four – and you’re persuading, not just writing.
DM me if you want to build smarter appeals.
#fundraising #npsky
You need a new lens.
Stop writing what would convince you.
Start writing for how they decide.
Feel. Path. Ask. Why.
Hit all four – and you’re persuading, not just writing.
DM me if you want to build smarter appeals.
#fundraising #npsky
You write one appeal – but it needs to speak to four donor types.
Story. Structure. Stats. Bold ask.
That’s not fluff. It’s strategy.
If your appeal’s falling flat, one of those is probably missing.
Reply “Checklist” and I’ll send the breakdown.
#fundraising #npsky
Story. Structure. Stats. Bold ask.
That’s not fluff. It’s strategy.
If your appeal’s falling flat, one of those is probably missing.
Reply “Checklist” and I’ll send the breakdown.
#fundraising #npsky
September 18, 2025 at 7:03 PM
You write one appeal – but it needs to speak to four donor types.
Story. Structure. Stats. Bold ask.
That’s not fluff. It’s strategy.
If your appeal’s falling flat, one of those is probably missing.
Reply “Checklist” and I’ll send the breakdown.
#fundraising #npsky
Story. Structure. Stats. Bold ask.
That’s not fluff. It’s strategy.
If your appeal’s falling flat, one of those is probably missing.
Reply “Checklist” and I’ll send the breakdown.
#fundraising #npsky
You write appeals that would convince you.
That’s the mistake.
Donors decide differently:
🧠 Stats
💼 Bold ask
🗂 Structure
💬 Emotion
The best appeals speak to all 4.
That’s how you connect.
DM me if you don’t know your default style.
#fundraising #npsky
That’s the mistake.
Donors decide differently:
🧠 Stats
💼 Bold ask
🗂 Structure
💬 Emotion
The best appeals speak to all 4.
That’s how you connect.
DM me if you don’t know your default style.
#fundraising #npsky
September 17, 2025 at 4:45 PM
You write appeals that would convince you.
That’s the mistake.
Donors decide differently:
🧠 Stats
💼 Bold ask
🗂 Structure
💬 Emotion
The best appeals speak to all 4.
That’s how you connect.
DM me if you don’t know your default style.
#fundraising #npsky
That’s the mistake.
Donors decide differently:
🧠 Stats
💼 Bold ask
🗂 Structure
💬 Emotion
The best appeals speak to all 4.
That’s how you connect.
DM me if you don’t know your default style.
#fundraising #npsky
That appeal was solid.
Strong case. Clear ask.
So why didn’t it land?
Most fundraisers write to the list – but only speak to one kind of mind.
I found a framework with 4 donor decision styles that changed how I write.
Reply “framework” & I’ll send it.
#fundraising #npsky
Strong case. Clear ask.
So why didn’t it land?
Most fundraisers write to the list – but only speak to one kind of mind.
I found a framework with 4 donor decision styles that changed how I write.
Reply “framework” & I’ll send it.
#fundraising #npsky
September 15, 2025 at 3:45 PM
That appeal was solid.
Strong case. Clear ask.
So why didn’t it land?
Most fundraisers write to the list – but only speak to one kind of mind.
I found a framework with 4 donor decision styles that changed how I write.
Reply “framework” & I’ll send it.
#fundraising #npsky
Strong case. Clear ask.
So why didn’t it land?
Most fundraisers write to the list – but only speak to one kind of mind.
I found a framework with 4 donor decision styles that changed how I write.
Reply “framework” & I’ll send it.
#fundraising #npsky
This job search tip is for the girlies: Apply like a man.
Men apply when they meet some of the criteria.
Women wait until they meet all of it.
If the job fits your goals and you’re halfway there? Go for it. You can learn the rest.
Ever landed a job you didn’t feel ready for?
#fundraising #npsky
Men apply when they meet some of the criteria.
Women wait until they meet all of it.
If the job fits your goals and you’re halfway there? Go for it. You can learn the rest.
Ever landed a job you didn’t feel ready for?
#fundraising #npsky
September 12, 2025 at 4:15 PM
This job search tip is for the girlies: Apply like a man.
Men apply when they meet some of the criteria.
Women wait until they meet all of it.
If the job fits your goals and you’re halfway there? Go for it. You can learn the rest.
Ever landed a job you didn’t feel ready for?
#fundraising #npsky
Men apply when they meet some of the criteria.
Women wait until they meet all of it.
If the job fits your goals and you’re halfway there? Go for it. You can learn the rest.
Ever landed a job you didn’t feel ready for?
#fundraising #npsky
Fundraising is a people job. You can’t show that in a PDF.
Want to break in? Network like it’s your job.
Ask for info interviews. Volunteer. Talk to people.
The fundraiser who builds relationships to get the job is the one who thrives in the job.
#fundraising #npsky
Want to break in? Network like it’s your job.
Ask for info interviews. Volunteer. Talk to people.
The fundraiser who builds relationships to get the job is the one who thrives in the job.
#fundraising #npsky
September 10, 2025 at 5:30 PM
Fundraising is a people job. You can’t show that in a PDF.
Want to break in? Network like it’s your job.
Ask for info interviews. Volunteer. Talk to people.
The fundraiser who builds relationships to get the job is the one who thrives in the job.
#fundraising #npsky
Want to break in? Network like it’s your job.
Ask for info interviews. Volunteer. Talk to people.
The fundraiser who builds relationships to get the job is the one who thrives in the job.
#fundraising #npsky
Want to work with donors someday?
Stop applying for jobs that won’t get you there.
If your goal is Major Gifts or CDO, don’t start in the back office.
Gift processing and data roles matter – but they rarely lead to front-line fundraising.
Start where you want to end up. (1/2)
Stop applying for jobs that won’t get you there.
If your goal is Major Gifts or CDO, don’t start in the back office.
Gift processing and data roles matter – but they rarely lead to front-line fundraising.
Start where you want to end up. (1/2)
September 8, 2025 at 3:03 PM
Want to work with donors someday?
Stop applying for jobs that won’t get you there.
If your goal is Major Gifts or CDO, don’t start in the back office.
Gift processing and data roles matter – but they rarely lead to front-line fundraising.
Start where you want to end up. (1/2)
Stop applying for jobs that won’t get you there.
If your goal is Major Gifts or CDO, don’t start in the back office.
Gift processing and data roles matter – but they rarely lead to front-line fundraising.
Start where you want to end up. (1/2)