Since launching his 2016 presidential campaign, Kentucky Republican Sen. Rand Paul has paid particular attention to traditionally left-leaning demographics. Paul was the first White House hopeful to appear on Snapchat, a social app used by millions of Millennials; the first to launch an initiative focused solely on soon-to-be or newly eligible voters, setting up more than 300 "Students for Rand" college chapters in just 30 days; and the first to host a fundraiser with leaders in the cannabis industry.

"In the last go around, President Obama won the youth vote 3-to-1," Paul said Wednesday during an interview with the Washington Examiner.

He went on, while fidgeting with a stack of sticky notes in the third-floor office of his campaign headquarters. "I think we sometimes seem to be the stodgy party, with balanced budgets, low taxes and less regulations. But when you talk to young people, they're like: 'I don't have any money.' So taxes and regulatory issues aren't as big a deal for them."

"The [National Security Agency] overreach and government overreach gives us a unique opportunity to be one of the leaders in opposing that program and actually getting things to go our way," Paul said when asked what messages he's using to cultivate support among young Americans.

"That, as well as criminal justice issues are big for us on a lot of college campuses," he noted, before taking a swing at establishment favorite, Jeb Bush. "I've talked about the hypocrisy of Jeb going to an elite Northeastern school and smoking pot, but then not really recognizing himself that the poor kid on the South Side of Chicago has a much higher chance of getting caught smoking pot."

"Arrests are about 15-to-1, black-to-white in Chicago even though uses are about the same," Paul said matter-of-factly, showing he's done his homework on an issue that's become central to his campaign.

The libertarian-leaning senator and son of former Congressman Ron Paul believes the issues dominating much of his rhetoric — criminal justice reform, marijuana decriminalization, privacy rights and wasteful government spending — are capable of exciting voters across generational lines.

Earlier this week he spoke to a room full of "the largest Republican donors in the country" about Kalief Browder, an African-American teen who spent nearly two years in solitary confinement at Rikers Island without ever being tried or convicted of a crime. Browder committed suicide in early June, just two years after he was released from the New York prison at age 19.

"I told them all the same stories about criminal justice, and I think they're hearing it," Paul said, adding that "there's not a large population of African Americans in a primary, but you don't have to be African American to know what justice is and what is unjust."

Paul says he constantly reminds people that if the Republican Party wants to expand its membership, it must first expand its messaging.

"We've to got to be a party not of just the Second Amendment, but also the Sixth Amendment – saying that we are the party of justice and everybody gets their day in court and everybody has a right to a trial before a jury," he said.

"When people understand that you can be a minority because of the color of your skin or the shade of your ideology, [they] can start to maybe put themselves in someone else's shoes," he added, noting that he's yet to find an audience where his outreach has hurt him.

"It helps to distinguish me as someone who might get votes in a general election which is ultimately what we want to do," Paul said.

At the moment, reaching the general election is looking like an increasingly remote possibility for Paul and his supporters. The junior senator from Kentucky, who ranks ninth in the Examiner's presidential power rankings, is fighting tooth-and-nail to "Defeat the Washington Machine" before it defeats him.

Many of the voting blocs Paul is trying to appeal to aren't a very big presence in Republican primaries, an electorate that skews older and whiter.

Ahead of the Federal Election Commission's fundraising midnight deadline Wednesday for candidates and their PACs, Paul staffers were strewn across the three-story rowhouse with frantically dialing donors.

"You've donated to Sen. Paul before … in June, that's correct. Would you like to contribute to his campaign again?" a young woman's voice could be heard saying from the second floor.

Twenty-four hours after Paul spoke to the Examiner, his campaign announced a total haul of around $2.5 million in the second fundraising quarter — less than half of what it raised between Paul's presidential announcement in early April and the July quarterly deadline on June 30.

Nevertheless, Paul seemed at ease when addressing his fundraising figures and bottom-tier position in the polls. He currently stands at roughly 3 percent in the latest RealClearPolitics polling average of Republican voters, far behind fellow Republican hopefuls Marco Rubio and Ted Cruz, who serve alongside Paul in the Senate. He attributes his low poll numbers, he said, to "a celebrity skewing."

"I already think there is a taste in the mouth of voters that is basically saying, 'We've about had enough.' I really think there is," Paul said. "There's been a crest and you're going to see a reshuffling of the deck, and we think we're posed."

In the meantime, the senator plans to ramp up his travel to early primary states, where he says he's "probably better organized than any other candidate," and communicate to voters the one message he hopes they'll hear loud and clear: "I want people to know that I'm a different kind of Republican. I can attract people from all walks of life, not just by believing the message we stand for, but by taking that message to places we haven't gone."

Paul added, "Five years ago, I was a local small-town doctor never elected to anything. So five years later, to be one of the 10 leading candidates for the presidency, I would say I'm amazed at where I am."