Donald Trump has mastered social media like no other presidential candidate before him, using it as a tool to make news and communicate with supporters. But the Republican nominee’s failure to turn his massive online support base into a robust fundraising tool is a missed opportunity, despite a new multimillion dollar investment many say is too little, too late.

Trump spent $8.4 million on digital consulting and advertising in July, his latest campaign finance report showed. That’s more than four times the $1.6 million he spent in June. The last two months have comprised 95 percent of what he’s spent on digital overall, and it’s nearly three times what he’s spent on far more expensive advertising on TV.

By those numbers, digital is Trump’s top spending priority. But half a dozen Republican and Democratic digital strategists told NBC News that putting together a last minute digital strategy will cost more — and net less — than one built earlier. And it may yield disappointing results.

Put simply: The boastful billionaire’s big play isn’t his smartest investment.

Related: Where will the Republican Party go after 2016?

“The irony here is, look, he could have saved himself a lot of money,” Republican digital strategist Patrick Ruffini said. The chairman of Engage LLC, Ruffini isn’t a Trump fan but argued that the Republican nominee could “have been outraising Hillary Clinton” if he had invested in digital fundraising early.

“Fundraising takes place in the inbox,” said Wesley Donahue, a Republican digital strategist who worked on Florida Sen. Marco Rubio’s presidential bid. “If you wait longer, then you’ve got to spend more.”

Candidates typically spend years building up an email database that they can then mine for donations for months and years, and some grow them by renting outside group’s digital lists — adding users who respond to their database — and running digital ads.


Democratic nominee Hillary Clinton’s list was built years in advance of her current White House bid, combining the list she built in her 2008 campaign with the 4 million person list built by the Ready for Hillary super PAC that was transferred to the campaign last year. Digital has scored a far smaller percentage of her spending: She’s spent more than $68 million on television ads, and $7.2 million on digital and online advertising since her campaign launched last April.

Online advertisements are relatively cheap — with the notable exception of a pricey promoted hashtag Trump’s campaign purchased in July — so observers say that a large portion of his digital budget is likely being used to buy and rent email lists from like-minded Republican groups. He then sends fundraising appeals to people on those lists, collecting and keeping the donations, and, perhaps more valuably, email addresses. While Trump’s team long boasted of the big data gathering their massive rallies’ RSVPs garnered, he wasn’t utilizing those lists for fundraising. He didn’t send out his first solicitation until June 21, 2016 — one year and one week into his candidacy.

It’s expensive to build a foundation quickly, Donahue said, and since small-dollar donors typically give repeatedly, they’re worth more the earlier you can get them on your mailing list.

“He’s just doing what he’s supposed to,” he said. “It’s about time.”

Trump’s digital strategy is just one of the things he opted out organizing of during the primary, only to later scramble to put one together. He entered the general election without a finance team or a fundraising arm; he has few staff in battleground states and has largely dismissed the modern data analytics used by campaigns to target voters. He’s staffed by a comparatively miniscule staff of less than 100, while Clinton has hired more than 700 staffers. The campaign says it is growing quickly, and argues that the nontraditional campaign just doesn’t need the kind of structures others need.

Trump’s digital team is — like many of his earliest advisers — from outside the Beltway. The firm orchestrating Trump’s digital strategy, Giles-Parscale, is run by a Trump associate, Brad Parscale, who did not respond to NBC News’ requests for comment.

Related: Hillary Clinton and Allies Outpace Team Trump in Fundraising

Parscale, a Texas-based digital strategist who is relatively new to politics, had been employed by the Trump Organization’s businesses since 2011. Faced with staffing a presidential bid at the last minute, he brought in some outside vendors, including The Prosper Group, to help staff Trump’s digital presence.

Vincent Harris, a digital strategist who worked very briefly for Trump this spring, said much of what Trump is doing others did a year or more ago.

“I worked for Sen. Paul and we were doing a lot of things they are doing now, back in the primary election,” the Harris Media head said. “But look, who won and lost?”

Kenneth Pennington, one of the strategists behind Sen. Bernie Sanders’ Democratic primary digital strategy, offered this perspective: “It’s possible Trump could have been a much better online fundraiser. He hasn’t made a real effort. When we were really competitive … we were edging up to $43 million [in online donations] a month.”

Sanders’ small-dollar fundraising was perhaps the most notable of the 2016 cycle: He raised nearly $135 million of his $231 million online.


Trump has also had online fundraising success compared to his lackluster traditional fundraising. He’s brought in twice as much from donors giving less than $200, much of it coming from online solicitations, but his late start has put him far behind Clinton. While her online fundraising is more than Trump’s — $60 million to Trump’s $37 million in online support — it’s only one-fourth of her total financial support. And much of Trump’s online solicitations are merchandise sails, from those iconic “Make America Great Again Hats,” for instance.

Of course, both Trump and Clinton have raised money online through their joint fundraising accounts with their parties but those numbers aren’t released until October. However, by focusing almost entirely on fundraising online, strategists say Trump may not have time or money to implement a digital strategy aimed at persuading undecided voters and energizing his base to get out and vote in November.

“It’s very simple: The digital strategy is raise as much money as possible,” Ruffini said. “As a result I don’t think other elements of their digital strategy will be as filled out or as effective.”

Persuasive messages may not raise money directly, but they help energize the base and may, crucially, get voters to the polls.

“If you’re Hillary Clinton and you have a lot of resources, you can allocate some to persuasion, unlike the Trump campaign, which has to focus exclusively on fundraising,” noted conservative digital strategist Joel Sawyer.

To wit: This summer, Clinton launched a Facebook ad to “Trump Yourself,” which painted Trump insults — “Total lightweight! Sad!” read one — on fans’ profile pictures. It boosted her brand’s presence online. Perhaps even more importantly, it also gathered email addresses along the way.