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James Sun
James Sun, a former “Apprentice” competitor, was featured as one of GeekWire’s 12 Geeks Who Give Back in 2011 when he was with Pirq. (File photo by Red Box Pictures)

In 2007, Seattle entrepreneur James Sun competed on season six of NBC’s reality television series “The Apprentice” with Donald Trump. The experience gave Sun a unique connection to and understanding of how the billionaire businessman thinks and operates.

Nine years later, Trump did not earn Sun’s vote in last week’s election. But, despite a campaign that ultimately turned Sun off and drove him to vote for Hillary Clinton, the president-elect does have Sun’s confidence going forward.

Donald Trump
President-elect Donald Trump. (Via andykatz / Bigstock)

That confidence is rooted in the belief that, in Sun’s words, Trump is a smart campaigner who did what he needed to do to ignite a particular base and win. And that ultimately, Trump will emerge as a moderate with the the ability to listen and learn, and defy the damning portrait that emerged of him over the long campaign.

GeekWire caught up with Sun this weekend as he was traveling in China and South Korea on business. In a lengthy Skype call, Sun shared his thoughts on Trump’s intelligence, what he was like on “The Apprentice,” Trump’s understanding of tech and his opinion of Seattle, the importance of cross-border commerce, and how dangerous it was for Trump to fan the flames of division among Americans.

More optimistic than most people

“This won’t happen to me. This won’t happen to America, right?” Sun says at the start of our conversation, equating Trump’s victory to the shock of having just been in an auto accident.

But he follows that by going where few of Trump’s detractors can right now, especially — in staying with his own analogy — if they’re still coping with being hit head-on by the reality of who the next president of the United States is going to be.

“I’m more optimistic about what’s going to happen than most people are,” Sun says.

Sun, 39, is an accomplished University of Washington graduate who is a well-known tech entrepreneur in Seattle. He founded the mobile restaurant deals site Pirq, which was acquired by iPayment 2 1/2 years ago, and he has a long list of companies and media properties which he has been attached to.

Sun was the first Asian male to star on “The Apprentice,” during a season which was filmed in Los Angeles. He ultimately made it to the final board room meeting, where he was fired by Trump in favor of another champion.

Like a large portion of the populace, Sun didn’t like what he was hearing from his former “boss” as Trump launched his candidacy for the Republican nomination, campaigned through and won the primaries, and ultimately took on and beat Clinton last Tuesday.

But he thinks there is more to Trump than his tendency to be a “straight shooter” who speaks his mind without thinking.

“Trump is not an idiot,” Sun says. “He will listen to people. … He’s the type of guy who would say an opinion, and he may not understand the whole set of arguments before he says that opinion, but then he will listen, and he’s willing to change his mind after listening.

“I’ve had personal interactions with him where he does listen, especially if the person is intelligent and if they have done something with their life.”

Sun calls Trump a “very, very smart marketer” who intentionally targeted a core group of voters with a message that appealed to their discontent.

“I’ve never met a guy who hates to lose more than Trump,” Sun says. “I’ve met a lot of people in my life but this man just disdains losing. He’s a winner in that regard. He knows how to win. Once he won the primaries, I think he legitimately wanted to be the president because he wanted to win.

“Now, did he fully understand the scope of what it means to be the president? Probably not. But now, I think he does.”

Sun says that as a 70-year-old father and grandfather, there is a human element to Trump that he doesn’t think has been sufficiently conveyed by the media.

“He’s still a human being,” Sun says, even mentioning that the president-elect likes Oreo cookies. “I remember having chats with him during ‘The Apprentice,’ and we talked about life, family. So he’s going to do the best that he can by listening to his confidants.”

But there’s an element of the population that was listening to Trump during the campaign and what they took away from his message is what troubles Sun right now. Trump supporters who have been emboldened by his tough talk on immigration or nationalism, for instance, are using his victory as a justification for hateful behavior, according to some reports.

“I am actually afraid of what’s happening, the news that I am reading about,” Sun says. “People that have racist beliefs are acting on them, they feel like they’re almost validated. That’s taking our country backwards.”

But Sun says that more than anything he wants people to understand, from his standpoint, that he believes Trump is not a racist.

“I’m a minority. I’m an Asian-American minority and I can look everyone in the eyes and say, ‘Trump is not a racist,'” Sun says. “However, his supporters were incited by a message of isolation, racism, bigotry. That’s why I actually did not vote for him. Not because I think he’s racist but his supporters created a message around that, and that goes against everything that I believe in. As a human being, as an individual, Trump is not racist. Therefore, I want every racist person in this world to know that that’s not who he is. If you think that you’re validated because he became president, you’re wrong because Trump’s not racist.”

In an interview with “60 Minutes” on Sunday night, Trump directly appealed to his supporters to stop harassing minorities.

“If it helps, I will say this, and I will say right to the cameras: ‘Stop it,'” Trump said.

But Sun does say that there is no sugar coating what was said on the “Access Hollywood” tape that came out on Oct. 7, in which Trump was caught in a lewd conversation admitting to sexually assaulting women.

“That audio tape was bad, no doubt about it. There’s no ‘oh, locker room talk’ — it was bad,” Sun says, adding that he can’t imagine another politician who would have been able to weather such a storm.

Sun says he personally never heard or witnessed, on camera or off, anything like what was said on that tape. He admits that Trump would frequently mention whether he thought a woman was beautiful, “but not in a derogatory way.”

Trump and tech

Plenty has been said about Trump’s view of the tech sector, whether it’s his threat to get Apple to make their products in the U.S. or his belief that Jeff Bezos is using his ownership of the Washington Post as a means of sheltering Amazon from burdensome taxation.

In regard to Trump’s own understanding of technology, Sun says that Trump has come a long way from when he interacted with him on “The Apprentice.”

“When I met with him the very first [time], he asked me, “You’re in the internet business, how do you guys make money?” He just didn’t understand the user acquisition model and then revenue later. Because if you think about it, he’s a traditional guy, real estate guy. But I told him, ‘Think about it like real estate. When you build a new building, you have to put $100 million into it before you recognize any revenue by leasing it out.’ So, when I explained it like that, he understood it much better.”

Sun thinks that Trump’s policies could be felt in a couple of different ways when it comes to tech companies, startups and venture capital.

“Because of his policies of corporate tax rates going lower, for companies that are acquiring companies it’s going to be a big benefit,” Sun says. “I think that acquisitions will actually increase. Therefore, VCs will like that because they’ll have liquidations that are preferable. Now, he will probably get rid of carried interest because he’s kind of anti-hedge funds, and hedge funds use that as a huge tax loophole, and it impacts VCs.”

On top of all that, things could get “dicey,” as Sun puts it when it comes to H-1B visas, which a lot of tech companies rely on to hire workers from India and China. “I do believe he’s going to restrict that,” Sun says. “Not 100 percent, but he’s going to make it harder.”

Despite what Sun considers to be Trump’s more traditional business sense, he says there’s no doubt that he learned a lot from him.

“As a startup person, Trump is a visionary. He literally even before he knows a plan, he will make a statement and see a vision of where he wants to go and he’ll just say it. A lot of startups might say, ‘Our mission is to change the world.’ He likes that. He likes bombastic statements — the big, hairy, audacious goal. Startups are going to have to change directions many, many times, but you still got to say that goal in order to recruit the right people, in order to incentivize, motivate, and let the market know who you are.

“Now, you might change your plans throughout,” Sun adds. “Amazon clearly probably never imagined one day it would be globalizing commerce all around the world — they were selling books in the beginning. But, I think, Jeff Bezos probably had that kind of a vision. I’ve never interacted with him so I don’t know. You almost have to act as if before you even get there. That’s something I learned from Trump.”

When it comes to Seattle, Sun says that Trump showed respect for the city back in 2007 when he would mention companies such as Boeing and Microsoft, which he would refer to as “great companies.”

“He thinks that we have a lot of talented, smart people in Seattle,” Sun says. “He said, ‘You guys might have some of the best, smartest, and most educated per capita in the U.S., with Boston.’ So he respects Seattle.”

Sun himself calls the city the perfect place to run the type of cross-border businesses that he’s interested in right now.

“Seattle is the perfect place for trade,” Sun says. “If you want to do cross-border and you want to to do e-commerce, Seattle is the place. We have Nordstrom, we have Amazon, we have Costco. We, obviously, have Microsoft. I think the tech talent in Seattle is loyal. Silicon Valley, there’s a lot of tech talent, but they’re not loyal. I think that Seattle represents the human capital potential of a true diverse city. I think that’s what keeps me in Seattle.”

Sun is currently the co-founder of AppZocial, which helps businesses have their own branded and targeted social communities outside of Facebook or LinkedIn.

He is also involved in three companies which are majority owned by his family, including: Dramabeans, a content site with a huge following in China that is dedicated to recapping Korean television dramas; W2 Beauty, an e-commerce site which markets Korean cosmetics to a global audience; and Nice Culture IT.

He thinks the worst thing Trump could do to, from a cross-border standpoint, is to close borders and put tariffs in place.

“In the next 10 years, China will be one of the biggest consumer markets in the world,” Sun says. “Maybe even bigger than the U.S. A lot of people are predicting that. The dumbest thing that the U.S. could do right now is, with all of the investment that we put into China, to not reap the rewards from it. Right now is the time for U.S. companies to start selling into China.”

‘Let’s heal the country’

This isn’t the first time Sun has spoken up about Trump. He was part of a group of former “Apprentice” contestants who came out in April to denounce Trump’s campaign of “sexism, xenophobia, racism, violence and hate,” as reported by Politico and other outlets.

In a statement at the time, Trump called the alums of his show “six failing wannabes” out of hundreds of contestants.

“Ask how successful they’ve been since they left,” Trump said, arguing that no one would know who they were if not for him. “They just want to get back into the limelight like they had when they were with Trump. Total dishonesty and disloyalty. They should be careful, or I’ll play hours of footage of them individually praising me.”

But in his interview with GeekWire, Sun made it clear that he is already of the belief that the best way forward for the country is by working together and supporting the future president.

His first step is to put together what he calls a “coalition” of minority-owned business leaders that have done extremely well in the world.

“I’m going to actually reach out to the Trump campaign and talk about the immigrant story, and why it’s so important, and how many jobs we’ve created as immigrants,” Sun says. “Trump will understand that, but I need that message to get out even deeper to his base to help unite our country. I literally started this two days ago. I got some very big names already agreeing to create this little committee to reach out and build bridges to the Trump campaign.”

And Sun knows it won’t be easy.

His biggest fear is that such a division was created during the campaign that many people are not going to want to give Trump a chance and Trump’s base is not going to want to do what’s necessary to meet Democrats and liberals halfway.

“Now that he’s the president, we have to reach out,” Sun says. “I want to say, ‘Look, Trump, here’s our story. Here’s all the jobs that minorities have created. When you need to reach out to the minorities, we have all these business leaders. Basically, let us help you to do that. Let’s heal the country.’ I want to support him because he’s our president now, right?”

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