In Silicon Valley, Democratic supporters among the tech cognoscenti seem to be as common as hoodie-wearing 20-somethings with dreams of being the next Mark Zuckerberg. A number of high-profile tech leaders signed on to a June letter endorsing Hillary Clinton, and 150 others wrote an open letter saying a Donald Trump presidency would be a "disaster for innovation." 

Yet some are taking a more creative approach at expressing their views. In the past week, Reid Hoffman, the co-founder and executive chairman of LinkedIn, has rolled out two attempts designed to — if not directly help Clinton — try and lure Trump to release his tax returns and spotlight the absurdities of this year’s election campaign.

On Monday, Hoffman, who signed the June letter endorsing Clinton, wrote a post on Medium sharing that he would help a 26-year-old marine’s campaign to get Trump, the Republican nominee, to release his tax returns. The Marine, Peter Kiernan, hopes to lure Trump into releasing his returns by promising to donate money pledged on the website Crowdpac to veterans organizations. Hoffman said he would match Kiernan’s effort by a multiple of five, up to $5 million. 

Then on Wednesday, Hoffman launched a satirical card game, Trumped Up Cards — think Cards Against Humanity or Apples to Apples with a 2016 election slant — intended to both spotlight the absurdities of this year’s election and get more people talking about the election. The deck goes for $20.16, and all proceeds will benefit nonprofit, nonpartisan organizations that Hoffman says “are already working to make America great.”

We caught up with Hoffman about his two efforts, what the billionaire entrepreneur thinks about money in politics, and why he believes more business leaders have a responsibility to get involved in the political process. The conversation below has been edited for length and clarity.

So you’re basically selling a kind of Cards Against Humanity for the NeverTrump crowd. Where did you get the idea?

I've been playing board games and card games my whole life. I’d played a lot of games — everything from versions of Dungeons and Dragons, everything else as a kid — and I’m familiar with the whole genre of comparison games. Cards Against Humanity. Apples to Apples. So I’d been thinking about creating one, actually about Silicon Valley, for a while. At the beginning of the year, my team and I were talking about the priorities of the year. And we’re like, “Shouldn’t we do [a card game] on Trump?” So we made one for friends. Then they said this should be much more widely available. We hustled to put out an appropriate public version. 

Where will the proceeds go, and who helped you take it from an idea to actual game?

I have a little team who works for me. They’re part of my team for a number of things -- everything from speaking at conferences to arranging events. The key thing was to try to make sure [the game was] kind of an inspiration, in line with things like “The Daily Show” and John Oliver. To realize you can both highlight the absurdities of the system — the absurdities of a reality television star running for president, on that being his credentials — together with actually learning something about the political election, all through the lens of satire.

Sure, the person who buys it is probably sympathetic. But it’s something you can play with your friends. It’s meant to be around the dinner table, around the living room, creating a social environment in which people talk to each other, encouraging that kind of conversation about what are our values, what should we be thinking, what is a qualification for being president. That conversation — held in a personal way — is precisely what I would love to see more of.

I will not make a single dime off this game. The proceeds, after paying expenses, will go to 501(c)(3) [organizations] that are already working to make America great. We’re working through that list. We’re actually thinking about doing a social media campaign, and have people voting for which ones. For example, I like organizations like Village Square, National Voter Registration Day, and 501(c)3)s have to be very broad-minded on politics. They can’t be partisan.

It’s quite a creative — and extensive — effort to help support a candidate, or at least critique her opponent. You announced another such approach this week, when you pledged to multiply a marine’s campaign to lure Donald Trump into disclosing his tax returns. Why did you do that?

I’m a great believer in democracy and American democracy — both its truth and its aspirations. 

Part of that is to say, an accurate and truthful picture about who you are is critical. That’s part of the reason all American candidates since the 1970s have released their income tax returns. It’s a form with which you cannot lie — or if you do lie to the IRS you’re in serious trouble — about what your business interests are, whether you have any conflicts of interest, whether you actually, in fact, go to extreme lengths to avoid paying taxes, whether you’re philanthropic. That’s a critical part of the character of a presidential candidate.

So how do you essentially challenge, in a high-integrity way, Trump to do the right thing?

It was like, well: Veterans have done great service to the country. The dedication of years and risk. Supporting them already is important. When we saw [Peter Kiernan's effort] on Crowdpac, we’re like 'okay, supporting this Marine and this cause is exactly the right thing.' 

As we looked at it we thought, "Trump himself has already done this." That even adds more credibility to that. Let’s call him out exactly the way he called President Obama out [in 2012, when Trump offered money to charity if Obama released his college and passport records and applications] and let’s make sure everyone’s aware of it.

What happens if Trump doesn't release his taxes? Are you looking to still make a contribution in some other way?

Most likely. I’d have to think about it. I’ve had a couple of friends who are heading veterans organizations say "So, will you donate?" And I say of course, I'll write some donations. But this challenge is to try to highlight to Mr. Trump that he should step up and do the right thing as a presidential candidate.

You have endorsed Hillary Clinton. Why are you taking this approach, creating set of cards, making a high-profile pledge, rather than just giving money to a PAC or to the campaign?

I’m a substantial direct donor to Hillary’s campaign. I have, on occasion, given to PACs to support various candidates, including President Obama, or issues. I would prefer that we live in a society with substantial campaign reform. So I prefer to do efforts that reinforce and highlight democracy, that highlight broad participation, that highlight awareness of the issues and lead to a wiser set of people.

I prefer direct and pro-democracy ways [of getting involved]. Whether they’re a satirical product, or a calling out of a challenge grant done by a Marine, as I see those, I will always prefer those ways, because I think they are better at supporting and reinforcing the health of the democracy.

You were an early investor in Crowdpac, a political web startup, which is hosting Kiernan’s challenge. Is your pledge in any way an effort to draw attention to Crowdpac? And are there any links between the card game and any of the companies you’ve invested in to disclose?

No links between the card game. On Crowdpac, I did lead their series A [round of fundraising]. [Hoffman's "social impact" investments, like Crowdpac, are done on a personal basis; if they return a profit, the proceeds go back into his family foundation.] 

I would have supported [Kiernan's] challenge anywhere I found it. I probably found it in Crowdpac because I happened to be looking, as I’m helping them with the company. I’d be delighted if it helps bring attention to Crowdpac because the reason I made the social impact investment is I actually think getting everybody involved, collectively, in politics — including the money in politics — is a way to reinforce democracy. 

I realize that both of these efforts are things you’re doing on a personal basis, and not as a representative of LinkedIn or Greylock. But do you wonder if there’s any risk in offending Republican employees who work at LinkedIn, or at some of the companies Greylock invests in?

I’m more cautious on the LinkedIn side. One of the reasons I posted my efforts on Medium is that it wants to be a source of intelligent discourse on the web. I did actually write a note to the LinkedIn company group to say, “Hey, normally you see me posting a lot on LinkedIn. The reason I’m posting this on Medium is to make sure we’re all aware that we have a politically inclusive culture on LinkedIn.” Even though I’m a very strong supporter of Hillary, I wanted to make sure everyone knew, tangibly, that I’m a supporter and a strong believer in our inclusiveness at LinkedIn.

In terms of the Greylock portfolio companies, if someone — an entrepreneur or executive or employee — doesn’t understand that one important role of leadership in our society, for all leaders, including business leaders, including investing leaders, is to help our democracy, then they’re welcome to take their business elsewhere. It’s an ethical and moral mandate for people not to try and be apolitical as business leaders but to try to help us get collectively to the right outcome.

I’d be unhappy if any workplace were saying, “If you work here, you have to vote Republican,” or, “If you work here, you have to vote Democrat.” That would be anti-American. I would hope they would say, “If you work here, we hope you will be an active citizen and we’d like you to be informed. We’d really like you to vote. We’d like you to have intelligent discourse with each other about voting the right way.” That is something I’m a very strong believer in.

Do you think tech leaders or wealthy entrepreneurs have a responsibility to get involved in the political process? Sounds like you do.

I do. I think one of the central things — an important lesson of leadership -- is that with power, comes responsibility. If you have power — money is power, positions of prominence and control are power, media is a position of power — if you have power, you have the responsibility to help the society grow and navigate in the right direction. Sometimes you can only do a little. How much you do is dependent on your own measurement of your own value. Your own ethics. But you should always be asking yourself, 'am I doing the right thing?' And I think it’s beholden that people say, 'look, I’m lucky to be an American. I’m lucky to be a Silicon Valley person, in my case. I should repay that luck by being a good leader.' And I think it’s an ethical mandate for absolutely every leader.

Seems like many business leaders are wary to get involved, because they want to position themselves well for whichever party wins, or they’re concerned about how an endorsement will be received by customers or employees. Do you think more business leaders should make their political leanings known?

Look, I want to be inclusive to my customers. I want to be inclusive to my employees. I want to be inclusive to my shareholders. Being inclusive, I think, is important. But if you take that to mean I’m being uncivic, or apolitical, then the society loses your leadership. I think it’s actually extremely important. They're relatively easy skills, to say, "Here’s how I can express express a point of view, a reasoning, for why it is that I think this is the right path for our country and this is the right path for this candidate, and why that is." That can be a healthy dialogue. That leads to our democracy getting better.

I disagree with Michael Jordan’s, "Well, Republicans buy Nikes too." ... I have many Republican friends. I’m a very strong advocate for Hillary, but one of my very close friends, Peter Thiel, is a strong advocate for Trump. That’s part of a healthy democracy. You lead. You have to be in the field in order to contribute. If you don’t contribute, you’re failing your responsibilities of citizenship.

Do you have more up your sleeve before November?

For sure, but I’m working on them. We don’t have an update. ... I'm planning on spending a bunch of time on it for the next couple of months.

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