LAS VEGAS - Andrew Yang was having lunch with eight recipients of his $1,000 monthly "Freedom Dividend" in a private poolside room inside the Bellagio hotel when one lucky winner offered up how he was pitching this unconventional presidential candidacy to friends.
"He wants to be your sugar daddy!" said Chad Sziszak, a 30-year-old from Ponchatoula, La., who planned to put his stipend toward car repairs and reconciling old debt.
"Wow I hadn't thought of that one," Yang replied, before adding his own characteristic deadpan: "I prefer the Asian Oprah."
The room burst into laughter.
It was another amusing moment in his quixotic, yet entertaining quest for the White House that has managed to outlast governors and members of Congress.
The 44-year-old entrepreneur, who is polling around sixth place in the Democratic field, has raised enough money to compete beyond the early primary states and looks to be having more fun with the process than just about anyone else. But he also had a confession to make.
"Like, I'm very proud of the campaign," he told this small group of supporters. "But I'm getting greedy and I want to win."
With just over two months before voting begins, Yang is confronting a crossroads that any outsider candidate comes to once they prove momentum and staying power: How to successfully convert a largely improvised and highly unorthodox internet-fueled movement into a credible option for the most important office in the country.
And for Yang, who relishes the revelry of the trail even as he delivers a sobering economic warning, the question is even more acute: Can a candidate who crowd surfs, embraces self-deprecating jokes and makes cameos in dark EDM music videos ever cross the necessary mainstream threshold to be taken seriously?
"The way that we get taken seriously is we continue to grow, we continue to outperform expectations," Yang said. "And the fact is, this a very, very fluid dynamic field. None of the frontrunners have pinned down a clear majority."
Yang's flagship campaign proposal - to provide every American with a universal basic income to combat what he predicts will be a wave of worker displacement caused by automation - has attracted an ardent national fan base (known as the #YangGang) whose zealous enthusiasm is reminiscent of Ron Paul's following in 2008 and Bernie Sanders' insurgency in 2016.
This singular focus has distinguished himself among the more than 20 Democrats who have pursued the 2020 presidential nomination and handed him a straightforward solution to a problem blind of ideology.
"Win, lose. This is actually something I'm really proud of," Yang told his "Freedom Dividend" beneficiaries, each who shared with him how they were going to use their newfound cash. "At the minimum, we improved a bunch of people's lives in a real concrete way."
But it's also opened him up to a perception that while the Yang storyline is fun watercooler fodder, it's not for real.
Carter Eskew, a Democratic media consultant who worked on Al Gore's presidential bid, believes it will be difficult for Yang to be seen as anything other than a niche candidate.
"Yang is really a single idea candidate - the dividend - which in fairness is his solution to a lot of other issues like ... health care costs, income inequality etcetera. But Yang's approach can come off as gimmicky, not unlike Herman Cain's 9-9-9 plan of the 2012 election," said Eskew.
The critique hasn't been lost on Yang's team, which is figuring out how to speak beyond the ballrooms of hardcore Yang Gang fanatics and toward the masses who still know little to nothing about him, perhaps other than he's an Asian man who likes math. One recent point of growth for the campaign has been the hiring of a veteran Democratic consulting firm, Devine Mulvey, Longabaugh to craft messaging.
To wit, Yang's first TV ads are standard political fare: Biography mixed with cornerstone Democratic issues like health care and the environment. One spot that intends to humanize the candidate features Yang's wife explaining the challenges of raising a son with special needs.
It's "getting people to take the second step to 'You're an interesting figure,' to 'Wait, you might be right,' to eventually voting for him. We're at the 'Wait, you might be right' phase I think right now," explained Yang's campaign manager Zach Graumann, who like Yang has no prior political experience and comes out of the start-up world. "The question is, as we're all wondering, how deep is the Yang Gang? Can we grow the polls organically with traditional Democrats?"
Yang himself is in the midst of debating these questions with his advisers. At the center of the internal campaign conversation is whether to double-down on his defining message of instituting a universal basic income or attempting to broaden beyond it to demonstrate presidential timber on a wider array of topics.
"There is a concern that I can just be the give-people-money guy and that it detracts from the overall perspective of the campaign and the overall vision for the country," Yang told McClatchy as he made his way through the Bellagio parking garage to head to a rally at the Rio hotel and casino, just off the Vegas strip.
"It's a debate we've been having," he went on to say. "My wife is a big fan of the dividend and just thinks we should lean into it and just keep on giving people money and think that's the way forward. There are people who have been in politics a long time who think that we need to try to broaden and humanize."
Yang's private-sector experience revealed to him a rapidly approaching world in which truck drivers and Ubers are replaced by driverless vehicles, clerical assistants and desk workers are switched out for cloud-based artificial intelligence and bartenders and store workers are supplanted by self-service kiosks.
MGM's hotel and casino in Las Vegas has already begun replacing bartenders with automated cocktail machines in an effort to shred hundreds of millions of dollars in labor costs. Handing over money to the masses, Yang's theory goes, would first provide stability during this economic convulsion but also allow for the freedom to pursue work that is more valuable and personally fulfilling.
"The automation wave is coming in part because if your sole goal is to get work done, people are much trickier to deal with than machines," he writes in his book, "The War on Normal People." "The challenge we must overcome is that humans need work more than work needs us."
As far as political strategy, Yang said he's genuinely torn on the best path forward. His announcement of the UBI pilot program at the September debate raised $1 million and netted 500,000 new email addresses. But he appears inclined to attempt to broaden his message. The conclusion may be born out of necessity, given what he sees as an ongoing battle to attract mainstream media coverage.
In the van ride over to the Rio, he notices #YangMediaBlackout trending on Twitter, a result of his supporters' outrage at MSNBC for leaving him off a polling graphic showing the latest result in Iowa. Data shows that Yang consistently yields the least amount of television coverage of any candidate. And at Wednesday's Democratic debate in Atlanta, he received the least amount of speaking time of any candidate - about half of what the frontrunners were allotted, according to a New York Times tracker. (Yang is currently one poll short of qualifying for the next debate in December.)
"It's quite confusing, man," he tells me, seemingly exasperated as he scrolled through his iPhone. "It definitely is (on purpose.) It happens really consistently."
He turns, offering me a fist-bump, "Thank you for not being part of the blackout."
But for Yang's supporters, the fact that he's completely comfortable in his own skin broaching issues from a non-political perspective is the allure.
"It only takes talking to you and getting the first check to realize it's not a gimmick, it's much more than that," Sziszak told Yang.
Backstage at the Rio, Yang is offering high-fives to staffers as Graumann licks his hand to place his candidate's hair in place. "Button your top button and then unbutton it when you sit," he instructs Yang.
When Yang hits the stage, more than 500 supporters leap to their feet. A group of men in #YangGang shirts rush to the front, chanting his name. Yang's body gyrates to the 90s hip-hop song "Return of the Mack," which is blaring over the speakers. Naturally, Yang dives into the crowd and makes a lap around the ballroom offering high-fives.
"The fact that he's willing to have fun when he's running for president, I don't think that's a disqualifier at all, in the age of Donald Trump and all the nastiness," said Mark Longabaugh, a Democratic strategist who recently signed on to craft Yang's television ads after working for Sanders in 2016. "He's a happy warrior. There's a lot of dour candidates out there in the field. And I think he's refreshing despite the fact that he has a very tough critique of our economy."
Once Yang returns to the stage and the crowd takes their seats, it's not long before he offers another unconventional policy proposal for a presidential aspirant.
"We should legalize online poker," he declared. "Is that a top 20 problem for people? No."
Screamed one member of the audience in response, "Yes!"
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