Jessica Cloud, CFRE | Real Deal Fundraising
@jcloudrealdeal.bsky.social
Tips to help nonprofits raise ⬆️ 💵
https://linktr.ee/jcloudrealdeal
https://linktr.ee/jcloudrealdeal
This is Dr. Stanley Hauer—brilliant professor, fierce thinker, and one of the sharpest minds I’ve ever had the privilege to learn from.
We were in England, deep in the stone stairwell of Bodiam Castle, and he was exactly in his element—bringing ancient stories to life with wit and precision.
We were in England, deep in the stone stairwell of Bodiam Castle, and he was exactly in his element—bringing ancient stories to life with wit and precision.
November 26, 2025 at 5:15 PM
This is Dr. Stanley Hauer—brilliant professor, fierce thinker, and one of the sharpest minds I’ve ever had the privilege to learn from.
We were in England, deep in the stone stairwell of Bodiam Castle, and he was exactly in his element—bringing ancient stories to life with wit and precision.
We were in England, deep in the stone stairwell of Bodiam Castle, and he was exactly in his element—bringing ancient stories to life with wit and precision.
This photo was taken the day I graduated. I had a Master’s in hand, a head full of literature, and a heart that had been reshaped by years of learning under remarkable professors.
But what you can’t see here is what made that moment possible.
But what you can’t see here is what made that moment possible.
November 24, 2025 at 8:28 PM
This photo was taken the day I graduated. I had a Master’s in hand, a head full of literature, and a heart that had been reshaped by years of learning under remarkable professors.
But what you can’t see here is what made that moment possible.
But what you can’t see here is what made that moment possible.
You ask donors to believe your mission is worthy.
But secretly, you’re still trying to prove you are.
That disconnect?
It slows your asks, your income, your growth.
You don’t fix it by pushing harder.
But secretly, you’re still trying to prove you are.
That disconnect?
It slows your asks, your income, your growth.
You don’t fix it by pushing harder.
November 24, 2025 at 5:54 PM
You ask donors to believe your mission is worthy.
But secretly, you’re still trying to prove you are.
That disconnect?
It slows your asks, your income, your growth.
You don’t fix it by pushing harder.
But secretly, you’re still trying to prove you are.
That disconnect?
It slows your asks, your income, your growth.
You don’t fix it by pushing harder.
You give all day.
To your team. Your donors. Your mission.
But when someone gives to you?
A compliment? A coffee? A thank you?
You freeze.
You deflect.
You rush to give something back.
That’s not humility.
That’s chronic over-functioning.
Burnout. Under-earning. Always not enough.
To your team. Your donors. Your mission.
But when someone gives to you?
A compliment? A coffee? A thank you?
You freeze.
You deflect.
You rush to give something back.
That’s not humility.
That’s chronic over-functioning.
Burnout. Under-earning. Always not enough.
November 21, 2025 at 4:15 PM
You give all day.
To your team. Your donors. Your mission.
But when someone gives to you?
A compliment? A coffee? A thank you?
You freeze.
You deflect.
You rush to give something back.
That’s not humility.
That’s chronic over-functioning.
Burnout. Under-earning. Always not enough.
To your team. Your donors. Your mission.
But when someone gives to you?
A compliment? A coffee? A thank you?
You freeze.
You deflect.
You rush to give something back.
That’s not humility.
That’s chronic over-functioning.
Burnout. Under-earning. Always not enough.
You ask donors to believe your mission is worthy.
But secretly, you’re still trying to prove you are.
That disconnect?
It slows your asks, your income, your growth.
You don’t fix it by pushing harder.
But secretly, you’re still trying to prove you are.
That disconnect?
It slows your asks, your income, your growth.
You don’t fix it by pushing harder.
November 19, 2025 at 4:30 PM
You ask donors to believe your mission is worthy.
But secretly, you’re still trying to prove you are.
That disconnect?
It slows your asks, your income, your growth.
You don’t fix it by pushing harder.
But secretly, you’re still trying to prove you are.
That disconnect?
It slows your asks, your income, your growth.
You don’t fix it by pushing harder.
You can have the best campaign plan in the world.
But if you sit across from a major donor and flinch when you ask?
It’s not because you weren’t prepared.
It might be because you didn’t believe you were allowed to receive that level of generosity.
But if you sit across from a major donor and flinch when you ask?
It’s not because you weren’t prepared.
It might be because you didn’t believe you were allowed to receive that level of generosity.
November 17, 2025 at 3:30 PM
You can have the best campaign plan in the world.
But if you sit across from a major donor and flinch when you ask?
It’s not because you weren’t prepared.
It might be because you didn’t believe you were allowed to receive that level of generosity.
But if you sit across from a major donor and flinch when you ask?
It’s not because you weren’t prepared.
It might be because you didn’t believe you were allowed to receive that level of generosity.
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