With Trump, There Is No Crystal Ball


NewCo Shift Forum Dialogs, in Partnership with Work Market

Political veteran John Heilemann frames the consequences of an unexpected election

John Heilemann

For more than 20 years, journalist John Heilemann has covered America’s presidential elections. He was the very first online journalist accredited by a presidential campaign (in 1996, by Bill Clinton’s White House, as a correspondent for Wired and Hotwired), and went on, with his colleague Mark Halperin, to write two New York Times No 1. best selling books on the 2008 and 2012 presidential elections (Game Change and Double Down). In the past two years, Heilemann has established himself as a quick-witted host on Showtime’s acclaimed documentary series The Circus, as well as Bloomberg’s With All Due Respect.

I asked Heilemann to help program and host NewCo Shift Forum’s political and policy track, and the result was fantastic — an intimate, off the record conversation with Obama senior advisor Valerie Jarrett, an on the record exchange with Clinton campaign manager John Podesta, and much much more. Below, Heilemann and I kick off the event — which convened just 15 days into the Trump administration — with a question: What on earth just happened?

John Battelle: How many of you have seen either With All Due Respect or The Circus? John Heilemann is the executive producer and creator of those two shows. The Circus is extraordinary — for those of you who haven’t seen it, it’s a weekly news documentary that covered the entire build up to the election.

The producers just came out with a documentary which debuted in Sundance a week ago and on Showtime last week called Trumped. JOhn and I are going to have a little talk about his role in organizing Shift Forum’s “National Interest” topic, which he is going to be moderating throughout the next two days.

John Heilemann: Thank you.

JB: John and I have worked together now for over 20 years. We’ve produced a lot of different events together…we worked on the Internet Summit in the ’90s. FourSquare, a technology, telecommunications, entertainment, and media event with Steve Rattner and (his firm) Quadrangle back in the day. Then Web 2 Summit. We did iDeals together, which was about the craze of deals in the Internet space. And now this. I appreciate you being here.

JH: I’m happy to be here. Just for the sake of everybody here, I know you want to spend a lot more time on this, but you gave a little bit of an overview of the inception of the idea for this conference. I still don’t fully understand what this conference is about, even though I’m part of it. I do remember thinking that I understood it when you first explained it to me nine months ago.

For the sake of everybody in the audience, spend a couple minutes unpacking the intellectual genesis of this conference, which is really different from any of the ones that you previously described, which are all straightforward business conferences. It’s a little different.

JB: This is definitely different. You were way ahead of me into policy and politics. John was, in fact, the first national affairs editor of Wired when I was part of that crew. You are way ahead of me in politics, but a year and a half ago, I realized that it wasn’t enough to be obsessed with the technology business, startups, exits, unicorns. I wanted to understand more broadly the impact of technology on society. It struck me that once you start to study that, the most rational actor in this space were businesses. Businesses needed to start to lead, needed to take responsibility for the authority and the power that they had been accrued.

This was a relatively new conversation that hadn’t been convened, which is how do businesses lead? Fortunately, there were a lot of examples of those kinds of businesses that were started in the last 5 to 10 years here in the Valley and around the world.

I thought it would be interesting to start a conversation about the role of business in society and, in particular, how policy relates to that because there wasn’t a very robust conversation between policy and business, particularly technology, at the level of an executive event. That’s where Shift came from.

JH: Right. That was all a time when we didn’t remotely think that it was possible that…

JB: Yes, I remember a dinner that I had with you in the spring. This was when Trump was marching through the primaries. I said, “He’s not going to win, right?” You were on the road. You were never home. You were always on a plane, always covering the election. You said, “Electorally, it’s just not possible.”

What the fuck happened? How did this happen?

JH: That’s a really good question. I don’t have an answer for it, though.

I want to actually…before we proceed on my little bit here, I want to — for the sake of getting the spirit of political engagement — do a little bit of a vote and get a sense of people in the audience. I’m going to ask you all to cast votes or give me a show of hands if you’re embarrassed voting in front of your seat mates or friends here, just close your eyes and the embarrassment will go away.

How many people in the room voted for Hillary Clinton for president? Hillary Clinton, that’s a lot of hands. How many people in the room voted for Donald Trump for president? That’s two I see. Three.

JB: Four.

JH: Four, OK. I have security for you guys to get out at the end of the event. I promise we’ll keep you safe on the way out. I should say congratulations. By the standards of San Francisco, this is a remarkably ideologically diverse crowd.


JH: I don’t have a good answer to your question, John. Part of what happened was the Democrats nominated the worst possible candidate they could have nominated in a year where people wanted fundamental change.

(FBI Director) Jim Comey, the Russians, polling being broken in a fundamental way. A lot of things happened, and we can talk about some of them over the course of the next couple days. But I do think that part of the reason why it’s relevant to have this conversation now, as you’ve suggested that we’re going to have at this conference, and I’m going to preview a little bit about how this is relevant here.

I think everyone would acknowledge, whether you’re someone who voted against Donald Trump but are willing to give him a chance, or whether you’re someone who absolutely hates Donald Trump and thinks he’s an existential threat to the country and everything you hold dear, is that we are in uncharted territory.

This a profoundly unprecedented moment for a couple of basic reasons that have nothing to do with anybody’s preconceptions or biases.

We have a president who is the first president in the history of the country who has no experience in government or the military whatsoever. He’s a businessman president, someone who got himself elected largely on the strength of having been perceived by millions of people as having been a tycoon, someone who built stuff, who did deals, who was a negotiator, had built a huge following.

25 million people a week used to watch The Apprentice. When he started the race, was someone who had a built in base of 25 million people who thought really well of Donald Trump, well enough that they would watch him once a week on television.

As we went around the country in the course of reporting on the election, you found a lot of people who basically knew Donald Trump from The Apprentice, and admired him. They thought he built things, and put his name on buildings, and that was kind of cool.

He’s brought this, whatever you think of his business skills and his acumen, that is a large part of how he ran. He doesn’t have those other sets of experiences but he brings those other, different skill sets and who is promising and already moving in very decisive ways to fashion a new kind of relationship between the White House and the business world.

That relationship, in his mind, largely centers around the industries…I don’t mean to sound pejorative about this, but the industries of the past. He’s talking about trying to revive the American manufacturing economy, trying to bring jobs back to the industrial Midwest, trying to revive the Rust Belt, to build things again.

He’s talking in the kind of terms where he wants to try to build up the industries that were the backbone of the American economy in the 1950s and 1960s and 1940s, and not being all that attentive to the industries, broadly speaking, of the future.

I did not think that we would so quickly get to the place where there’s this big, bright line in the sand where not only is there a space where Trump is not particularly attuned to a lot of the industries represented here and people who live out here, but where there’s this open hostility that’s now opened.

There was a moment in December, at least, where the tech industry tried to go to Trump Tower and say, “We want to work with you.” We now have most of the tech industry, almost all of it, signing off on what is, in many ways, an unprecedented legal challenge to one of the president’s first signature moves in policy on the immigration front, on the travel ban that, as John alluded to earlier, is out today.

The Court of Appeals is going to hear oral arguments on that tonight by phone. The Court of Appeals is here in San Francisco. There’s going to be a ruling on that by tomorrow morning, we think. We either will be headed to the Supreme Court or not.

The fact that the tech industry is now, very rapidly, moving into a position of oppositional resistance. People hear this talk about the resistance in America. The grassroots progressive left building momentum around being in open opposition to the President of the United States is a pretty unusual thing, especially only 15 days into the new presidency.

The fact that the most dynamic, innovative, forward thinking part of the American economy seems to be joining the resistance, is a really big deal and promises to be, when you talk about leadership and how the ways in which business is becoming not just a part of shaping the broader discussion around policy and politics but also, in this case, framing up a giant political debate that’s going to on in a sustained way over the course of the next two years, and over the next four years as we get to the midterms and the presidential elections.

We’re going to talk about all that. The other thing that’s unusual about Trump is that he’s not a Republican or a Democrat in any meaningful way. He was a guy who gave money to Democrats for years and years, who I think on many, many social issues agrees with most people in this room. Doesn’t actually care about things like abortion or gay marriage at all.

He is a nationalist, is a…

JB: If he could hear you, he’d be tweeting at you right now.

JH: He would be. It wouldn’t be the first time.

He’s something else. He’s a nationalist. He’s a populist. But he doesn’t naturally fit into either party ideologically. On economic policy in particular, in areas like trade, debt, deficits, entitlement reform. A million things, almost none of the things that he believes are the things that Republicans have believed for the past 40 or 50 years. And yet, Democrats are obviously not on his side on almost anything.

JB: How does the traditional Washington Republican establishment, in your world, the world that you swim in every day, respond to this?

JH: Most Republicans sit around and think that between Paul Ryan and Mitch McConnell there’s a Republican agenda that they hope, with Donald Trump’s acquiescence, that they can get enacted. They look at many of the other things, some of which have to do with his temperament, personality, the way in which he is now attacking federal judges, doing things that they find appalling.

They will speak out occasionally but in the end they still think that Trump is a vehicle by which they could pass tax reform plans they like, and pass other measures that they think are part of the more traditional Republican orthodoxy. Whether Trump will accede to that or not is an open question, but it opens up the door to a really interesting discussion.

To the point of this conference, over the course of the next couple days we want to talk about what the Trump administration and broadly defined Trump and his however temporary, however transactional alliance with the established Republican party, what does that mean for the technology industry in any significant sense.

What does it mean in terms of regulation? What does it mean in terms of not just immigration but on a variety of other issues? What happens to technology and innovation in a world in which Donald Trump is the dominant political actor with a bunch of friends on the Republican side controlling the House and Senate?

We want to ask what the new Trump economy looks like more broadly, not just for technology, but for business in general. As trade policy shifts, as immigration policy shifts, as a variety of other kinds of policy shifts, as Trump practices a kind of industrial policy that any Democrat who practiced it would be trashed for.

Browbeating CEOs, bribing CEOs, using the bully pulpit, in a way, to pick on particular companies. To get on Twitter or other places and pick particular CEOs and publicly shame them or induce them or exhort them to do what he wants. Again, something that we’ve never really seen before.

I was talking this morning to Valerie Jarrett. She said that she could not remember a single time in eight years where Barack Obama ever called out a single CEO of any company that she could remember. Industries, yes, but never a single CEO of a single company. Trump’s already done that half a dozen times even before he became President of the United States.

That’s an interesting environment in which to run a company, for obvious reasons.

We want to talk about business, the business environment, and the economy under Trump. We want to talk about the technology industry under Trump. Then, to your last point that you mentioned in your spot piece, I think super important for the long run and part of the reason why we have John Podesta, some technology people, some legal people here, is to go back and look at the hacked election.

The thing that happened in October with Russia having gotten involved in the American electoral process has huge implications for the future in terms of how we run our elections, but more broadly, how we run our government. The questions of cyber security, how we protect our most valuable cyber infrastructure from being penetrated by adversaries, not just Russia but others that are trying to do it all the time.

All those challenges are huge things that have economic consequences, technological consequences, and, as it turns out, as we learned in this election, have huge political consequences.

We want to talk about all those things. That is all the stuff that fits underneath the broad tent of our National Interests programming block.

It will all be really funny, too. There will be jokes in every panel. This will not be an exercise in kale eating, although I know I’m here in San Francisco so people like kale.


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