Week 18: September 15-21

This week was the calm before the storm, with all the campaigns sucking in their breath before one final scream before the end of Q3. Next week, my inbox will take a beating. This week, it endures.

As always, the square is when I gave donations to the campaigns.
If email volume matched the polls…

At 24 emails, Kamala Harris still managed to be America’s most vocal candidate even after toning down her 5/day strategy. Cory Booker was hot on her heels with 21 emails, though, and Joe Biden was immediately behind with 20.

This is not how emails usually go…

Somehow, this week, the email volume actually decreased day by day, except for Friday, which was full of activity. Usually, Sundays and Mondays are pretty slow, while Thursdays and Fridays are the busiest.

Every possible ask was asked.

Despite the unusual daily spread, the ask spread covered all the possibilities. Between Julian Castro’s campaign wanting me to sign his birthday card and Beto O’Rourke wanting me to forward his gun buyback petition around, even the rarest asks were covered.

More than twice as many fundraising emails as the next highest volume.

Even with all the asks covered, it was no surprise that the topic kept coming back to fundraising. The end of September is more than just an end of month deadline, it is also an end of FEC quarter deadline. Campaigns will be expected to turn over their numbers to the FEC for transparency.

Bernie Sanders is already trying to set his bar low.

Shortly after next Monday’s FEC deadline, the TV networks will take fundraising figures reported by campaigns, sort them from biggest to smallest in an on-screen graphic, and declare who’s winning the election from the numbers next to the dollar signs.

To the media, it doesn’t matter if your tens of millions of dollars come from billionaire casino magnates at fancy fundraisers, or from one million working people.

But it matters to Bernie. And it matters to us. And we bet it matters to you too.
Our problem is that despite having one million donors, our average contribution has fallen. A lot. It’s about $16 this month.

And with time running out before our deadline, we have to do everything in our collective power to meet our ambitious fundraising goals. So that is why we must ask:

Can Bernie count on you to make your first $2.70 contribution to our campaign? We know we have the people — and now we can show that we are just as powerful as the billionaire class.

We know that we have FAR more people who have made FAR more contributions to our campaign than anyone else in the race does. That includes Donald Trump — the sitting president.

But you’re not going to hear that from the corporate media. They just care about the total money.

The media won’t stop to think how incredible it is that our campaign can stay competitive all because of teachers, Amazon warehouse workers, Walmart cashiers, and Starbucks baristas who chip in a few bucks whenever they can.

We don’t know how we’ll stack up against the money raised from fancy fundraisers, billionaires, and health insurance executives. But we’re still going to do our damndest to make sure we come out on top if we can. So it’s up to all of us.

Please chip in your first $2.70 — or whatever you can afford right now, whether it’s less, or if it’s more — to make sure we don’t fall behind our billionaire-backed opponents.

You should be very proud of how we are raising money in our race for president. We will be able to transform our country because of working people. Thank you for being a part of this movement.

Team Bernie

I do feel the need to point out the spelling of “damnedest.”

I also need to point out that while the contribution deadline is on Monday, September 30, campaigns are actually given a couple of weeks to pull their numbers together and submit them to the FEC. I believe the filing deadline is actually October 15 or thereabouts. This means that probably the only campaigns who will have numbers the media can report on shortly after Monday are those campaigns who have their acts together or those campaigns who are incredibly pleased with their intake: see Pete Buttigieg from Q2.

All of that aside, let’s take a closer look on Sanders’ email there.

Sanders cares where his money comes from. It matters to him that it comes from working class people.

But it is bad that his average contribution has fallen a lot to $16 this month. He says himself, this is “our problem.”

He is proud that we have more people.

But media cares only about the total money. Media doesn’t care about the people chipping in the few bucks they can afford when they can.

Sanders wants to come out on top, so he needs me to give more money.

He doesn’t care about the total money. He just cares about the total money.

He’s proud that his donations are from workers giving what little they can spare, but he’s upset that he has a low average contribution amount.

We should be proud that he has the most number of donors out of all the candidates, but also, he needs more contributions.

There is a saying, you can’t have your cake and eat it too. It’s actually not correct. You absolutely can have a cake, and then you can eat it.

The accurate saying is you can’t eat your cake and have it too. Once you eat your cake, you no longer have your cake.

Sanders is trying to eat his cake (all working-class Americans!) and have it too (higher contribution average!). This creates a dissonance in his messaging that really rubs me the wrong way every time I read it. Because this isn’t the first time Sanders has been upset that his working-class Americans (who are crippled by student debt and medical debt, as Sanders continually reminds us) aren’t giving him the big dollar donations that people who can afford big dollar donations are giving his opponents. He will say, in the same email, that taking big checks is bad, but his checks are too little.

He is, every time he sends an email like this, putting his supporters in a no-win scenario. In the same breath he praises them for their donations, he also scolds them for not being good enough. Every time I get an email like this from Sanders, it infuriates me.

Remember to divide by 2 for most of these numbers

At least Sanders pauses to thank me frequently. Not that it absolves him from the catch-22 he throws around, but he is consistently the best at giving me thanks.

Both Joe Biden and Kamala Harris have been paying attention to the news around Sanders, and both of them have notified me about his million donors.

Folks, Bernie Sanders just announced he’s raised a staggering $47.5 million in 2019.

With that much money, ANYTHING could happen in this race.

So now, Joe Biden needs your help at this critical moment. Our mid-month deadline is only 24 hours away, and we are still 12,100 donations short of our goal. We can’t fall short.

If you want Joe to win the Democratic Primary, give $5 to this email. Every dollar gets us closer.

Team Joe

Oh, wait, sorry. That email came from August 16. Here’s the actual email.

Folks, Bernie Sanders just announced he has 1 MILLION donors to his campaign.

With that much money, ANYTHING could happen in this race.

Joe Biden needs your help at this critical moment. Our next deadline is on Saturday, and we are still 6,000 donations short of our goal. We can’t fall short.

If you want Joe to win the Democratic Primary, give $5 to this email. Every dollar gets us closer.

Team Joe

…you can understand my mix-up.

At least Kamala Harris was more original in her words, instead of recycling an earlier email.

CBS: “Bernie Sanders’ campaign announced Thursday it has now received contributions from over 1 million individual donors.”

We need to level with you — Bernie’s fundraising advantage is real. We need you to pitch in to help us catch up. But we don’t need to out-raise them: we need to out-work them. Donate here, if you can afford to »

This week, Bernie’s campaign boasted about having more than one million donors backing his campaign.

That’s a lot…

Bernie’s advantage in this primary sums up our challenge: every major frontrunner in this race has either run for president before or announced with a massive campaign war chest already in the bank.

It’s going to take all of us working hard to overcome the advantages candidates like Bernie Sanders have in this primary. Can Kamala count on your support to do it? Chip in now:

Team Kamala

However, while Biden and Harris worried about Sanders having so much money, Cory Booker was just worried in general. Over the last week, his emails steadily grew more desperate. This was from September 15:

Team — the deadline to reach our $250,000 goal is tonight, and we’re still $82,619 short. Here are my top three reasons why we can’t miss this goal, and why we need your help to do it:

1. Cory won the debate in Houston. Period. He proved that he deserves to be among the frontrunners, and can hold his own.
2. We have to file a quarterly report with the Federal Election Commission at the end of the month. This public report will be used to separate the frontrunners from the rest of the pack, and it’s crucial we show strong numbers.
3. The next debate is right around the corner. The stage will be even more crowded now that Tom Steyer has qualified, and that means we need extra resources to ensure Cory stands out.

Addisu Demissie, Campaign Manager, Cory 2020

September 16:

After last week’s debate, my team set a goal to raise $250,000 by midnight on September 15th.

Team, I’m writing to let you know that we’re extending our deadline to midnight tonight.

Cory Booker

September 17:

Team — I’m sorry to be emailing you again, but it’s important. Last night was the deadline for our $250,000 goal, and we fell $29,792 short.

We already fell short once this quarter. And with the FEC fundraising deadline quickly approaching, now is not the time to do it again.

Will you chip in right now to help us raise the remaining $29,792 of our goal by tonight, September 17th, at 11:59 p.m.?

Cory Booker

September 18:

Friend — I know I’ve reached out before about our mid-month deadline but I need your help. Can you help us close the gap on the $6,849 that we’ve fallen short by midnight tonight?

We’ve already missed a fundraising goal once this quarter. Setbacks like these directly impact how we continue — reaching voters about our campaign message and the work I’ll do as president — and frankly, they aren’t an option for us.

Cory Booker

September 19:

It’s almost that time.
In 11 days, we’ll be closing the books on our current fundraising quarter and filing a report with the FEC. When we report our financial numbers publicly, we need to have a strong showing. There are some candidates in this race who have massive online donor networks or the ability to self-fund a campaign. We need to be able to keep up our fundraising with candidates who have those advantages. Can you chip in today to help us meet our end-of-quarter goal?

Addisu Demissie, Campaign Manager, Cory 2020

September 20:

We’ve been called the underdog in this race — and it’s true. The fact is, I’ve never run for president before. And I didn’t enter this race with a huge network of donors from all over the country. And, any minute now, the DNC is going to introduce new debate qualifying thresholds.

So, I’m going to cut to the chase — we need a strong showing to prove that we’re in this until Election Day 2020, no matter the donor or polling thresholds that are thrown at us. Will you chip in right now to help our campaign have the resources it needs to win?

Cory Booker

On Saturday, September 21, Booker put his cards on the table.

In a moment, I’m going to ask you to donate to my campaign. I know you get emails like this from us and others all the time. This one is different. I’d like to explain why.

We need to raise $1.7 million by September 30th to make the immediate investments necessary to continue building a campaign that can really win. The next ten days will determine whether I have a path in this race. To be completely transparent with you, team, I’m only going to continue running if I see a clear path to victory.

This isn’t an end-of-quarter stunt or an attempt to spin the press. When we realized we were going to come up short of the resources necessary to grow, I knew we had a choice. So here’s what’s going on — no BS:

It’s now or never to continue building a campaign that can win — can you chip in $5 to help our campaign reach the $1.7 million we need by the end of the month? Here’s a link to donate:


Voting won’t begin until February, but the choices we’ll have then are being determined right now.

If you’re all in for me (thank you!) — if you haven’t settled on a candidate but you think I bring an important perspective to this campaign, if you believe the Democratic field should include someone like me who represents a low-income, majority-minority community, or if you want to have a choice in this primary beyond the current top four most-resourced candidates — then, please, consider making a donation toward our $1.7 million end-of-quarter goal.

A few moments ago, my campaign manager sent a memo about the state of our campaign and our decision to be radically transparent about our next steps to our staff, endorsers, and friends. I want you to hear what it says, too, so it’s copied at the bottom of this email. Please read on to hear more from Addisu — and know how grateful I am for your support today and every day.

Now or Never: Radical Transparency about the Next 10 Days of This Race
To: Cory 2020 Supporters, Friends, and Staff
From: Addisu Demissie, Campaign Manager, Cory 2020
Date: Saturday, September 21, 2019

Cory Booker decided to run for president because he believes that the only way to beat Donald Trump and heal our country is to bring people together — and he’s the best person to do that. He’s never been in this to raise his profile or to sell books. He is in it to win it.

The next ten days will decide whether or not he can.

We’ve known since the very beginning that he entered this race with some challenges — he didn’t have the near-100% name recognition of some candidates who’ve been on the national stage before, nor did he enter the race with tens of millions he could transfer from other campaign accounts.

What Cory has always had is the ability to inspire Americans to work towards a better, more united America — and to make us believe that our country can tackle its biggest challenges if we come together. As the only candidate in the Democratic field who goes home to a low-income, majority-minority community, Cory is able to speak with uncommon moral clarity about the pain of Americans who feel left out and left behind, while reminding all Americans that our common pain can only be addressed by reigniting our sense of common purpose. That has been at the core of who Cory Booker is since he entered public life over two decades ago and has been the driving force behind this campaign since Day One.

We know that when people hear Cory’s hopeful message and vision for a post-Trump world, he wins them over. We’ve seen it consistently throughout this campaign, and we’ll see it again later today during his speech at the Polk County Democrats’ annual Steak Fry in Iowa.

Here’s the real talk: We have reached a critical moment, and time is running out. It’s now or never: The next 10 days will determine whether Cory Booker can stay in this race and compete to win the nomination.

How We See the Race — No BS
Democrats’ historically strong, diverse field is about to narrow dramatically, and despite his unique message, political skills, and growing popularity nationwide and in the early states, Cory Booker might not be in this race for much longer — the same is true for other important voices in the field.

While we invested early in building an outstanding organization in our Newark headquarters and the February early states, other campaigns have, in recent weeks, surpassed us in scale and begun spending on paid persuasion efforts online and on television.

Between that and the likely increase in the DNC’s debate-qualifying thresholds, which would require significant funds to meet, it is probable there are only four campaigns in this race with the money necessary to build and sustain the national organization needed to win the nomination.

I’ll be blunt: We aren’t among them today, but with your help, we can be.

Our Opportunity: Now or Never, Together
Cory 2020 has the resources necessary to continue on as we are now for quite some time, but that is not enough. Cory is one of only 11 candidates who have qualified for the DNC debate in October, but that is not enough, either.

We have to change our fundraising trajectory right now — before September 30 — or we will not be able to grow our operation fast enough to win.

Rather than posture or pretend, we want to give our amazing supporters — and everyone who thinks Cory is a unique, important voice in this race, whether or not he’s their final choice yet — the chance to step up in this moment when they still have a chance to determine what the final field of candidates will look like.

Here’s the bottom line: Cory 2020 needs to raise an additional $1.7 million by September 30 to be in a position to build the organization necessary to continue competing for the nomination. Without a fundraising surge to close out this quarter, we do not see a legitimate long-term path forward.

September is traditionally one of the strongest fundraising months for presidential campaigns. But after a surprisingly positive August, we simply have not witnessed the expected uptick in fundraising over the last three weeks.

To put it bluntly, we need to scale our operation up in October and November to remain competitive and need a strong September to make that happen.

We need to maximize support from our current donor base, and we need to seal the deal with supporters who like Cory but have been waiting to contribute because of an assumption that they can wait until later.

Well, “later” is now.

If we do hit our goal, we believe we will ultimately win the nomination because of the early investments we made in talent and infrastructure — investments that have put us in the game to date and already paid off with Cory earning significant endorsements and support from elected officials and key activists in early states and beyond. We know this will further bear fruit when the majority of voters tune in and make up their minds later in this race; according to an NBC/Wall Street Journal national poll this week, 91% of Democratic primary voters have not made up their minds about which candidate they are supporting.

But now is the time to build upon what we’ve done, not to sit back and be complacent.

I want to be clear: This isn’t an end-of-quarter stunt or another one of those memos from a campaign trying to spin the press. This is a real, unvarnished look under the hood of our operation at a level of transparency unprecedented in modern presidential campaigns.

Raising $1.7 million in just ten days is a herculean challenge, but it can be done. After entering the race on February 1, Cory 2020 raised $1.4 million in the final ten days of March to close out the first quarter of this campaign. We need to do it again (and more!), and we need you to step up to the challenge.

It can be done — but only if we do it together.

Cory got in this race to win it and to beat Donald Trump. With four and a half months until voting begins, he is well-positioned to do just that — if he has the resources to support and grow our team. But if our campaign is not in a financial position to grow, he’s not going to continue to consume resources and attention that can be used to focus on beating Donald Trump, which needs to be everyone’s first priority in this election.

What We Need To Stay In This — and Win
If you’re all in for Cory Booker —

If you haven’t settled on a candidate, but Cory’s on your list —

If you think we need a choice in this primary beyond the current top four most-resourced candidates —

If you believe that the race for the Democratic nomination needs the perspective of someone who actually lives in a low-income, majority-minority community —

If you simply think Cory has an important voice and message that more voters should hear — here’s what this means for you:

Help raise the $1.7 million needed before 11:59 pm on September 30.

This is the moment to act. If you wait, it will be too late.

Voting might not begin until February, but the choices that Democrats will have then are being determined right now, and Cory needs your help today.

Here’s what you can do:

Donate. We literally cannot wait for support to come later. Go to corybooker.com/together to donate today. Many of you have given before — please give again today.

Join the fight. Text TOGETHER to 40203 to get daily updates between now and Sept. 30th about our progress to goal and how you can help.

Build the team. Encourage your friends, family, and neighbors to chip before the September 30th deadline to ensure Cory can stay in this race. We’ll have resources at corybooker.com every day you can use to spread the word.

Cory Booker/Addisu Demissie, Campaign Manager, Cory 2020

The email sent by Addisu doesn’t exactly read like an internal memo to me: it definitely sounds written for an outside audience. However, Booker has been struggling to raise money. Since the debate on September 12, he has consistently missed his $250,000 goal, pushing the date back again and again. Booker has not been one for cries of missed budgets and the world will end if I don’t help him out now, so I’m prone to trust that this cry for help is real: if he can’t raise the funds, he won’t continue with the race.

The thing is, Booker has pointed out that dropping out would be to help the field as a whole. If the energy for him isn’t there, then it would be selfish of him to continue to draw on any resources that any more favored candidates could benefit from. Rather than stay in a doomed race to further his own brand, Booker would drop out to strengthen the eventual nominee.

We have at least nine other candidates who could use that lesson. That actual humility.

And it is actually because of that show of selflessness that I threw Booker some extra dollars. I feel his upbeat attitude and voice urging unity is actually very important in this race, and I’d love to have it continue at least a little longer.

Since he sent that email, I’ve received updates that he’s raised nearly $200,000 and is feeling hopeful again. We’ll see if he can maintain his upward trajectory.

As the quarter draws to a close, though, many candidates are warning me about the incoming flood of emails, including some from themselves. I’ve covered those in the past. However, Pete Buttigieg sent me an email warning about more emails coming not about fundraising, but instead about his 4-day all-access bus tour across Iowa and his upcoming appearance at the Polk County Steak Fry.

Sure enough, Buttigieg sent an email with photos of the enthusiasm from the steak fry. As of Saturday, he was the only candidate to send me anything about this, other than Booker and Joe Sestak saying they’d be there.

Are campaign cowbells a thing?

However, the week was wrapped up by an email from Lis Smith, Buttigieg’s Senior Communications Adviser.

If you haven’t heard of Lis Smith, she is a powerhouse. Thanks in large part to her, I’m paying more attention to the names that sign off all these political emails.

I’ve been talking with Pete about this all-access media bus tour for MONTHS. It’s most campaigns’ nightmare — having press with you on the road 24/7 with no filter and no barriers. But then again, most campaigns don’t have a candidate like Pete.

From the beginning, we’ve run an unconventional campaign. We’ve gotten this far by being fearless and by disregarding some of the outdated rules of modern presidential politics. We’ll win this whole damn thing by keeping it up.

Besides, Pete places a premium on transparency. He says as much in just about every email to you. He wants to do the same with the press, too.

Maybe for any other communications adviser that would be a nonstarter. But with Pete? Have at it, I say. To know Pete is to like him and to understand that he is a once-in-a-generation candidate. That’s why everything on this bus tour is “on the record” and public information — because we want as many people as possible to see the Pete we get to see every day.

Having the media along for the ride is really just an added bonus. What matters most are the conversations we have in every Iowa community along the way of this bus trip. It’s about caucus-goers getting to know Pete. Because when they do, they’ll like him. His message will hit home with them. And his vision for the country will resonate with them. Take it from someone who met Pete and immediately became obsessed with the idea of working for him. And here I am — ready to win the presidency.

So here we go. Today’s the day. Pete and I are kicking things off in Newton and heading to Boone tomorrow. And while the next few days may be about Iowa, what we do here can translate to other states, too. New Hampshire. South Carolina. Nevada. California. You can help us keep it up and build the campaign by making a donation now.

In fact, you may have noticed this is my first email to this team. And because it’s my first, I want some results that will blow my teammates out of the water. 10,000 donations by the time the bus tour wraps up? Sounds bold enough to me — and every single one of those donations will help us build a campaign with the resources to win. In Iowa. In New Hampshire. In South Carolina and beyond. Send a donation our way now to make it happen.

Thanks, and stay tuned for more updates from the road. Keep your eye on Twitter for comments from the press, too!

Lis Smith, Senior Communications Adviser, Pete for America

I think I have a new favorite email writer.

“Disregarding some of the outdated rules of modern presidential politics.” I think this has been the real secret to Buttigieg’s massive success, at least with emails. Candidates like Joe Biden, Michael Bennet, and Andrew Yang all apologized for how many fundraising emails I was going to get, acknowledging that they were part of the problem. Yang even said:

I know we’ve been sending you a lot of fundraising emails lately. It’s the reality of a presidential campaign, but I wanted to take some time to talk about being on the road with Andrew.

Zach Graumann, Campaign Manager, Yang 2020

Buttigieg threw pleading fundraising emails out of the window completely. Just because it’s the traditional way of doing it doesn’t mean it’s a good way to do it.

Remember, Buttigieg scored the biggest Q2 fundraising haul without spamming my inbox full of arbitrary deadlines. Maybe he has a point about not following the old playbooks just because that’s what was always done…

Cory Booker has pulled into 2nd place, behind Joe Biden.

If you’ve enjoyed what you’ve read so far, consider supporting me on Ko-Fi. But Their Emails! merch is also available on for purchase here!

2 thoughts on “Week 18: September 15-21

  1. Lis Smith’s email is amazing! I loved it, and just wanted to throw away some cash, until I remembered I couldn’t! See, that’s some powerful person. Making you feel itchy to grab your VISA card, even when the FEC says you shouldn’t bother. Really wishing them well for this Q3 deadline.

    And thank you for your insight with Bernie’s mails. This thing has been bothering me too. Why ask people with limited resources to send you their spare dime buy making them feel guilty about the fact that their not-showing up allows the billionaires to rule? That being said, I’ve never been more willing to be part of the billionaire class than right after reading that mail.

    Finally, I’m pretty curious about how Booker’s last gambit will play out.

    Another fun read. Thank you!

    Liked by 1 person

    1. Lis, like Chasten, is one of Buttigieg’s secret weapons that should be deployed sparingly for best results!

      Sanders has recently sent an email stressing that you should only donate what you can afford, but still, his focus on his average donation is so disgusting to me. Either you want big donations or you don’t, but be consistent!

      I am definitely interested in how Booker’s Q3 numbers turn out. I’ll keep you all updated!


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