Andrew Yang — the crowd surfing, “Cupid Shuffling” 44-year-old entrepreneur whose cure-all for America’s economic ills is to give every citizen $1,000 a month — is easily the most unconventional candidate in the 2020 field.

Yet Yang, once dismissed as an entertaining sideshow, has shot past sitting senators and former cabinet secretaries to the sixth position on the last debate stage.

His theory of the last election is that automation forced so many people out of their jobs and caused so much anxiety that they were ripe for the picking by a different, um, unconventional candidate. Democrats need to connect with those voters this time, he says.

Yang spoke with POLITICO reporters and editors this week as part of a series of interviews with Democrats 2020 hopefuls. He dished on a range of topics, interspersing serious talk about his ideas with humorous observations about what it’s been like for a true political neophyte to run for the highest office in the land. Here are some highlights, edited for clarity and conciseness.

On why Democrats lost in 2016 and why he decided to run

“If you'd just turn on cable news why would you think Trump won? Russia, racism, Hillary Clinton, emails, Facebook, and the FBI. And it's ignoring the fact that we're in the midst of the greatest economic transformation in our country's history — the fourth industrial revolution. And that is just set to accelerate.

I saw all of this unfolding in 2016, 2017, and I understood my country did not understand what was happening. And so I decided to run for president. And as you all know, I'm now sixth in the national polls and I'm going to win this whole election.”

On his recent rise in the polls and the prospects of a nontraditional candidate

“What I find shocking is that Donald Trump could run the table in the Republican Party and become president and that people still believe that everything is essentially as it was. That in order to run for election successfully you need to be an elected official, that you need to talk a certain way, dress a certain way, be a certain sort of person. I mean objectively I have outperformed sitting senators and governors and congressmen and women that have been preparing to run for years in many cases . And so you have to ask yourself, ‘Is it harder for someone to go from total obscurity to sixth in the polls beating senators and governors, or from sixth in the polls to first?”

On whether the age of presidential candidates matters

“I do think that it's something we might want to look at — trying to figure out whether there's some standards we should have for the presidency. To me, if you were running for office at a particular point, then maybe it would be reassuring to the American people to have some sort of third-party [medical] evaluation.”

On getting his “Freedom Dividend” — or universal basic income — plan through a Republican-held Senate

“I want you all to play out this scenario: I shock the world, I become the nominee, I beat Donald Trump, I am your president in 2021. I come and say, 'Look, ‘I'm here because of the dividend. Let's get money into the hands of the American people.’

What we have is a Republican set of legislators that will have to then make a call and say, ‘Am I against a dividend that's going to help rural areas, that's going to help areas that have been blasted away by automation?’

Can you imagine Mitch McConnell's office when he goes back to Kentucky and the people there are saying, ‘Hey Mitch, why aren't we getting this dividend?’ Can you imagine a legislator's office or their phone lines if they were the person standing between their constituents and the dividend?

Money is very difficult to demonize. And after the money is in people's hands then we can start to reverse this mindset of negativity and scarcity that's weighing us down and making it harder for us to get things done.”

On claims that his $1,000 a month campaign giveaway violates federal law

“As you can imagine we have a small army of very smart lawyers who signed off on this. No. 1, if my campaign were to give a million dollars to a media company like POLITICO or to paid consultants down the street or to an army of paid canvassers, everyone would think that's completely OK. But if we give the money to individual American citizens to do whatever they want with, then it's somehow problematic. Campaigns like mine pay people all the time for any of a host of services. So let's say we were to give a thousand dollars a month to an American citizen and say, ‘Your job is to tell your neighbors and friends how you spend the money.’ That's actually essentially a marketing function on behalf of the campaign. And we're simply paying you the thousand dollars just you can tell your story so you can think of them as a variant of like a marketing consultant or a paid employee.”

On which American military interventions he's agreed with the past 20 years

“My three-part test for military intervention is, No. 1, are there vital American interests at stake or can we avert a humanitarian disaster? No. 2, is there a clear and defined time-frame for our intervention? No. 3, are our allies engaged and ready to assist? If those three things are a yes then I would be open to foreign intervention on a military basis.

Pressed for a specific answer, Yang said: "I'd say Kosovo, yes. And Afghanistan. Now Libya's a closer call. I'd have to I'd have to review some of the facts on that."

On his support from the technology sector, despite his attacks on automation

“We have at this point hundreds of people who work in the technology industry that are supporting my campaign and this is despite the fact that I'm very open about calling out the fact that technology is disrupting many of the jobs and industries in this country. Because they're not bad people for the most part. I mean some of them are assholes, but whatever.”

On whether he'll keep telling Asian jokes, which have offended some people

“We're a very diverse community and if Asian-Americans disagree with my response to a particular issue or a joke I tell, that's something I would expect and accept. You know, that that's what happens in a diverse community. I don't see any reason to dramatically change anything.”

On whether the Democratic National Committee’s debate thresholds are fair

"I was about to tell an Asian joke. (Laughter.) I'll tell it, why not. (More laughter.) I'm Asian so I love tests. You can tell I haven't changed my behavior.

The DNC’s threshold to make the debates have been incredibly helpful because then you just know what to aim for. So we need 130,000 donors and that's what we got. We needed 2 percent and that's what we got. If you look at the folks who did not make the thresholds, a clean half of them started their campaigns very late in the day. I mean like you parachute in the last minute and then you don't make the thresholds and then you're like, ‘These thresholds are unfair.’ Well maybe you should have shown up before July or whatever the heck month it was.”

On candidates attacking each other at the debates

“You watch these debates and you don't come away inspired about the direction of the country and being like, ‘Oh yeah, like, we've got this.’ The feeling people get is the feeling I describe, which is like, ‘What are these people yelling at each other about?’

There is this sense of manufactured outrage and rehearsed attack lines. You think to yourself, ‘Does that person really care what Joe Biden said 40 years ago?’ I'm essentially a proxy for the American public. I find the process to be very false and somewhat misdirected.

It's someone who's on the border of the polls or lowish who takes a pot shot at someone above them in the polls in hopes of elevating themselves. Could you have predicted that Julián Castro was likely going to attack Joe Biden? Yes. That's why it feels like we're in a stage show. And imagine being me on the stage show looking around and being like, 'Wow, like this is it?'"