It's an approach that seems to work so far: In addition to the large crowds O'Rourke has attracted, he raised US$6.1 million ($8.9m) during the first 24 hours of his campaign, a record-setting haul that narrowly tops the amount announced by Senator Bernie Sanders and dwarfs everyone else in the 2020 Democratic field.
During an unsuccessful Senate campaign in Texas last year, O'Rourke pioneered a new way for Democrats to run for office by holding hundreds of town halls across the state, answering thousands of questions, broadcasting his life on social media, raising record amounts of money from everyday voters and being relentlessly optimistic.
His presidential campaign is an expansion of that effort. He even kept the same logo, replacing the words "for Senate" with "for America."
As a presidential candidate, O'Rourke has heavily focused not on specifics but on two sentiments: positivity and humility.
He has pledged to lead by example and not invest in misleading ads or demean his opponents, even praising former Vice-President Joe Biden, who could soon join the race. Although O'Rourke is openly critical of Donald Trump's policies and rhetoric, he is careful to not personally attack the President.
O'Rourke admits that he doesn't have the answers to the nation's biggest challenges and is far from a perfect candidate. He has acknowledged that being a wealthy white man has given him privileges not afforded to all Americans, apologised for "really hateful" things he wrote as a teenager and promised to stop joking about how his wife is raising their three young children with only occasional help from him.
Some voters say they find O'Rourke's openness refreshing. "Sincere," said a longtime activist at his first campaign event in Keokuk, Iowa. "Inspiring," said an Illinois woman at the same event. "Easy to listen to," one of her friends added. At other events, other voters added more descriptors: "Genuine." "A regular guy." "Earnest." "Trustworthy."
"He's just so positive - that's what I like," said Olga Sanchez, 70, who drove more than two hours from the Des Moines suburbs to Waterloo to see O'Rourke speak and deliver a campaign donation. "He's not saying 'straight Democrat,' he's not saying 'independent,' he's not saying 'just progressive,' and he's not saying no to 'Republican' - that's just it, he includes everyone. . . . I'm all for inclusivity."
O'Rourke, while not completely void of policy ideas, spends much more time detailing the challenges facing the country than suggesting fixes.
At each campaign stop, he urges questioners to suggest their own solutions, although they rarely do, and often ends his answers with a call for a national conversation.
On gun control, O'Rourke continued to propose a ban on the sale of new assault weapons and the implementation of universal background checks, while also speaking emotionally about the toll of gun violence, particularly on children.
On the high cost of college, he reiterated ideas long pushed by Democrats - such as forgiving the student loans of public servants and creating debt-free higher-education options - while noting the crushing toll such debt has on many young Americans.
On healthcare, O'Rourke suggested adding Medicare to insurance marketplaces and giving states another shot at expanding Medicaid, while stating that a solution will be reached only by bringing "everyone into the conversation."
On immigration, O'Rourke has suggested giving citizenship to undocumented immigrants who have long called America home and increasing the number of refugees allowed into the country each year, but has also said he's still collecting ideas.
He has promised to protect abortion rights but has not detailed what needs to be done to reverse restrictions placed by Republicans. He has called for higher teacher pay and greater investment in public education, but has not suggested a funding source. He warned voters that they need to find a "bold" solution to climate change in the next 12 years, but he doesn't yet know what that will be.
O'Rourke told reporters that he plans to keep up the pace of several events each day and campaign in states that Trump won in 2016. He said the experience has confirmed his belief that Americans are eager for someone to heal the country's divisions.
"This campaign has got to be about learning from the people we meet and then finding a way to bring everyone together," O'Rourke said. "So I think this pace and this manner of campaigning is not just, perhaps, the best way to win. It may be the only way to serve if we're going to meet the challenges before us."
