DeSantis’s Risky Strategy: Trying Not to Trick Small Donors

In the months before the 2020 presidential election, Roy W. Bailey, a Dallas businessman, received a stream of text messages from Donald J. Trump’s re-election campaign, asking for money in persistent, almost desperate terms.

“Have you forgotten me?” the messages read, Mr. Bailey recalled. “Have you deserted us?”

Mr. Bailey was familiar with the Trump campaign: He was the co-chair of its finance committee, helped raise millions for the effort and personally contributed several thousand dollars.

“Think about that,” Mr. Bailey said recently about the frequency of the messages and the beseeching tone. “That is how out of control and crazy some of this fund-raising has gotten.”

He did, ultimately, desert Mr. Trump: He is now raising money for Gov. Ron DeSantis of Florida, whose campaign has pledged to avoid the kinds of online fund-raising tactics that irritated Mr. Bailey and that have spread in both parties, particularly the Republican Party, in recent years as candidates have tried to amass small donors.

No phony deadlines, Mr. DeSantis has promised donors. No wildly implausible pledges that sizable contributions will be matched by committees affiliated with the campaign. And no tricking donors into recurring donations.

This strategy is one of the subtle ways Mr. DeSantis’s team is trying to contrast him with Mr. Trump, who has often cajoled, guilt-tripped and occasionally misled small donors. Although his campaign has not directly called out Mr. Trump’s methods, on the day Mr. DeSantis declared he would run for president, his website prominently vowed to eschew “smoke and mirrors,” “fake matches” and “lies” in its fund-raising.

For the DeSantis campaign, the vow of no trickery is risky. Mr. Trump, the most successful online Republican fund-raiser ever, has shown that such tactics work. But Generra Peck, Mr. DeSantis’s campaign manager, said that approach damaged the long-term financial health of the Republican Party because it risked alienating small donors.

“We’re building a movement,” Ms. Peck said last month in an interview at DeSantis campaign headquarters in Tallahassee.

So far, it’s difficult to tell if Mr. DeSantis’s approach is working. His fund-raising slowed after his campaign began in late May, and campaign officials did not provide figures that would have shed light on its success with small donors.

The battle to raise money from average Americans may seem quaint in the era of billionaires and super PACs, which have taken on outsize roles in U.S. elections. But straight campaign cash is still, in many ways, the lifeblood of a campaign, and a powerful measure of the strength of a candidate. For example, G.O.P. presidential contenders must reach a threshold of individual donors set by the Republican National Committee to qualify for the debate stage, a bar that is already causing some candidates to engage in gimmicky contortions.

To highlight what it bills as a more ethical approach to fund-raising, the DeSantis campaign has devoted a giant wall inside its modest office to scrawling the names — first name, last initial — of every donor to the campaign, tens of thousands of them so far.

It is an intensive effort. During work hours, campaign staff members — as well as Mr. DeSantis himself, in one instance — constantly write names on the wall in red, blue and black markers.

“We want our staff to look at that wall, remember who supports us, to remember why we’re here,” Ms. Peck said.

Mr. DeSantis’s advisers argue that being more transparent with donors could be a long-term way for Republicans to counter the clear advantage Democrats have built up in internet fund-raising, largely thanks to their online platform ActBlue, founded in 2004. A Republican alternative, WinRed, didn’t get off the ground until 15 years later. A greater share of Democrats than Republicans said they had donated to a political campaign in the last two years, according to a recent NBC News poll, meaning the G.O.P. has a less robust pool of donors to draw from.

“One of the biggest challenges for Republicans, across the board, is building out the small-dollar universe,” said Kristin Davison, the chief operating officer of Never Back Down, the main super PAC supporting Mr. DeSantis.

The tell-the-truth approach to deadlines and goals has been tested by other campaigns, including those of Senator Bernie Sanders, who built a durable network of grass-roots donors in his two presidential runs.

Mr. DeSantis’s campaign said last week that it had raised $20 million in his first six weeks as an official presidential candidate, but the amount that came from small donors will not be apparent until later this month, when campaigns file second-quarter disclosures.

The campaign did not respond to a question about how many small donors had contributed so far. It had set a goal of recruiting 100,000 donors by July 1, but as of late June, the wall had only about 50,000 names, according to a fund-raising email.

And although Mr. DeSantis’s team has pledged to act transparently when it comes to small donors, senior aides in the governor’s office have faced accusations that they inappropriately pressured lobbyists into donating to his campaign.

Eric Wilson, the director of the Center for Campaign Innovation, a conservative nonprofit focused on digital politics, said the DeSantis campaign was wise to avoid online pressure tactics, which he likened to a “dopamine arms race” that burns out donors and turns off voters.

“They can be effective, but voters say they don’t like them,” Mr. Wilson said. “You can’t make the entire meal around sugar.”

Mr. Wilson said he had also seen other campaigns try more honest communications: “You are starting to see a recalibration.”

For instance, the campaign of former Gov. Nikki Haley of South Carolina said in May that Mr. DeSantis had imitated language used in Ms. Haley’s fund-raising emails.

The ways that campaigns reach out to potential small donors online grew out of old-fashioned telemarketing and fund-raising by mail. Before email, campaigns sent out fake telegrams, letters stamped to appear they had been hand-addressed, surveys and other gimmicks to draw donations.

In the era of email and smartphones, it is easier to reach a large number of prospective donors, but the risk of bombarding and overwhelming them is higher. It can also be harder to induce people to open messages, let alone contribute. The subject line has to be compelling, and the offers need to stand out — which can lead, for example, to dubious promises that campaigns will somehow “match” any contributions made, a practice that has been widely criticized.

Mr. Trump’s campaign sends about 10 emails per day, in addition to text messages. His campaign has escalated bogus matching promises to the point of absurdity, telling donors that their contributions will be matched at “1,500%.”

A spokesman for the Trump campaign did not respond to a request for comment.

The tactics aren’t limited to Republicans. Democratic groups have also been criticized and mocked for vague promises of “300 percent matches” in their fund-raising pitches.

For its part, the DeSantis campaign said its strategy was devised to establish long-term relationships with small donors, rather than to suck them dry as quickly as possible.

The DeSantis campaign has adopted a “subscriber exclusive” model, allowing donors to join so-called tele-town halls with Mr. DeSantis (“You guys are part of the team,” the governor told listeners during a June 12 call), gain early access to merchandise, and receive weekly “insider” updates. It’s the carrot, not the stick, a blueprint that campaign officials said was adopted in part from the business world.

Mr. Trump’s campaign has clearly taken notice.

On Friday, in an apparent round of fund-raising one-upsmanship, the Trump campaign announced a new donor initiative, saying it would build a “big, beautiful Donor Wall” at its New Hampshire headquarters.

“And I don’t mean scribbled on the wall with a crayon, like some other campaigns do,” said the campaign email, which was written in Mr. Trump’s voice, “but a heavy, respectable plaque with the names of our great donors finely etched within.”

All for a donation of $75.

Patricia Mazzei contributed reporting from Miami.