Democratic presidential campaigns are embracing some novel tactics to keep their digital fundraising programs humming as the cash race has taken on new importance this cycle in large part due to debate stage donor thresholds.   

From meet-it-or-go-home fundraising goals (see Cory Booker and more recently Julian Castro) to cash prizes and other norm-bending appeals, campaigns at all levels might just be able to take advantage of these tactics after the Democratic primary ends next year.

But which tactics have staying power and which are bound for the trash heap?    

The first question for campaigns down the ballot should actually be one of compliance, said Michael Toner, a partner at Wiley Rein LLP and a former chairman of the Federal Election Commission: “You’ve got to be careful. Whatever you say in your fundraising appeals has got to be factually accurate.”

One gambit that is now commonplace: a fundraising appeal that includes a contest element, for instance, Pete Buttigieg’s ask for a donation of any amount to “enter a contest” where the winner meets Chasten Buttigieg and sees “Hamilton” in San Francisco. It’s a model the Obama campaign helped develop and President Trump is also using.   

The caution for federal campaigns below the presidential level is to ensure the event actually goes off as advertised. If it’s just a ploy ahead of a deadline or to boost a single fundraising campaign, it may run afoul of campaign finance law.  

“As long as they’re careful and they actually have the [events],” Toner said, it wouldn’t be a compliance problem.  

This cycle that contest element has been taken a step further by Democratic presidential candidate Andrew Yang, who has pledged to “personally” give “up to 10” winners of his campaign’s sweepstakes $1,000 a month for a year. Yang called it a “Freedom Dividend.”

“I personally think that’s problematic,” Toner said. The concern there is that it raises “personal use questions.”

For instance, the Yang campaign would likely need to 1099-MISC the recipients, and may not be operational when that paperwork needs to be filed.  

Another former FEC chair agreed with Toner. “If such a program came to a vote while I was still on the commission, I would say the program violated campaign finance regulations,” Ann Ravel, a former FEC commissioner-turned candidate herself, wrote in September.

Some consultants were more appreciative of Yang’s ploy.

“That was genius,” said Cheryl Hori, founder of Pacific Campaign House.

Hori, a digital fundraising expert, noted that Yang’s campaign received nearly half a million email sign-ups during the Sept. 12-19 promotion.

Those emails, she said, are “a bargaining chip for building political power,” even if not all of them are actual voters, Yang supporters or Democrats.

One tactic Hori didn’t like: Beto O’Rourke’s recent fundraising appeal with the subject line “Amy Klobuchar.”

Part of the email read “Amy Klobuchar locked down her final requirement and officially qualified for the November democratic debate. Beto still hasn’t qualified,” the campaign wrote in an Oct. 24 email asked for a $3 contribution.

Candidates often go to great lengths to not say their opponent’s name — even during a live debate, but in the heat of the 2020 primary, the O’Rourke campaign isn’t the only one that hasn’t shied away from leading their fundraising appeals with the names of other Democratic hopefuls.    

“I would never want to give air to another candidate on my candidate’s dime,” Hori argued.

She also questioned if down-ballot candidates can capitalize on the tactic that Cory Booker popularized: needing an injection of cash or dropping out of the race. Down ballot, said Hori, “I don’t know that there’s going to be enough buzz generated.

“Part of the reason the Booker move worked was that he had a large audience and a large soapbox to project that message from.”

Threatening to drop out can also conflict with the message, “’I’m in this, I’m fighting for you, for this district.’”

Booker’s gambit paid off and now rival Julian Castro has followed suit. He told supporters last week that he would drop out of the race if he didn’t raise $800k by the end of October.

Count Andy Amsler of the Democratic fundraising firm Mothership Strategies among the strategists who are willing to embrace that sort of strategy.

“To be honest, more Democrats should be saying this and fundraising on these terms,” said Amsler. “It is a race for dollars and they’re in the fight of their lives.”

Donors need a reason to give and the threat to drop out is as good as any, he said.

“‘I’m in it to win it’ is great mobilization language. For donors I think it’s more effective to give them goals, to give them reasons to donate that money,” said Amsler, whose firm is working with Montana Gov. Steve Bullock (D) on his White House run. “You have to find the ‘hook’ to be able to do that.”

Still, Amsler noted that even in a desperate cash-or-drop-out plea, the dollar goal has to be attainable.

“If people feel that it’s an insurmountable goal, people aren’t going to donate,” he said.