The democratic socialist candidate for president is very good at raising money. In 2016, Bernie Sanders hauled in more than $228 million. This week, he proved that prowess was no fluke, collecting nearly $6 million in the 24 hours after announcing his 2020 bid, obliterating the previous high mark of $1.5 million for Kamala Harris. And the fact that the vast majority of those dollars came in small batches is a healthy thing for participatory democracy: four years ago, 58 percent of Sanders’s contributions were less than $200. This year’s cash came from 225,000 donors sending an on-brand average of $27.

None of Sanders’s opponents are scared by those numbers, however. Because what Sanders was less good at in 2016 was spending his large pile of money to win votes. Particularly the crucial Democratic primary votes of women and African-Americans. Especially in the key state of South Carolina. And three years after being crushed by 47 points there by Hillary Clinton, with an even more challenging field of primary rivals shaping up, Sanders is showing little sign that he’s going to get it right this time around. True, in January he spoke in South Carolina on Martin Luther King Jr. Day. Sanders has also taken every opportunity to blast President Donald Trump as a racist. Yet Sanders remains remarkably awkward on the subject: when asked about the candidacies of Stacey Abrams in Georgia and Andrew Gillum in Florida, he declared that “there are a lot of white folks out there who are not necessarily racist who felt uncomfortable for the first time in their lives about whether or not they wanted to vote for an African-American.” Symone Sanders, a strategist who worked for Bernie’s 2016 run, was puzzled by another recent comment that attempted to be high-minded yet came out sounding strangely demeaning. “He has this odd riff, about how candidates can’t just be a woman or a person of color,” she says. “Some people have said it’s tone-deaf—I think it’s a jab, and it’s not something that appeals to women or black voters.”

Joe Trippi is deeply familiar with the problem. “This is a very similar thing to what happened with us in the early stages of Howard Dean’s campaign in 2004. Vermont is not the most diverse state in the country,” says Trippi, who was the chief strategist for the surprisingly successful insurgent run by Vermont’s former governor. “In fact, I think it’s [one of] the least diverse. So part of it is just going into those communities of color and talking with people and learning. Dean did that, and over time he connected. The Vermont experience hampers Bernie, and I’m not sure that he’s figured out how to get beyond it. And it’s going to be even tougher with more diverse candidates out there competing for the votes he desperately needs to add to his coalition to have a real shot at the nomination.”

Sanders certainly recognizes the challenge. Yet he’s done little mechanically to address it, so far. There are no African-Americans in the ranks of his senior 2020 campaign advisers, and he has struggled to hire a top black organizer to run his South Carolina operation, where in 2016 he lost 84 to 16 percent among black voters. “I see signs that the senator understands the work that needs to be put into winning black votes,” says Symone Sanders, who ran Bernie’s 2016 South Carolina organization, and who was frustrated by the lack of support from the campaign’s leadership. “His biggest misstep was that he didn’t spend enough time in the state. It was like pulling teeth to get him to leave the Senate to go campaign. Now he’s done events all over the country that pay attention to the black electorate. But there are only four people who know how to run a winning statewide operation in South Carolina, and three of them are already working for someone else. Bernie’s people courted Jalisa Washington-Price real hard to run South Carolina, and she went with Kamala Harris.”