The Gray Area with Sean Illing

I could describe this podcast, and I will. But the tl;dr is this is one of my favorite conversations so far, and you’re going to enjoy it. So just go listen. Chris Hayes is, of course, the host of the MSNBC primetime show, “All In.” He’s also the author of the new book “Colony in a Nation,” as well as (the extremely prescient) Twilight of the Elites. But beyond the bio, Chris is a crazily smart and insightful thinker on US politics and society, and he's in rare form here. Among our topics:• The way Donald Trump’s success represents both the problems of elite power and elite weaknessWho even counts as an elite, anyway?How people decide what to trustThe difficulties of trying to approach politics with decency and charity in the age of TrumpWhy the key to “law and order politics” isn’t law, but orderThe underestimated power of humiliation in daily American life, and during America’s foundingHow Chris would cover Trump if he were a White House correspondentThe ways in which the media actually can be unfair to TrumpWhy the fight between Trump and the press is more a staged WWE-match than an actual warThe power of seeing politics as a zero-sum competition, even when it isn’t oneAnd much more. This conversation is dense and it’s fast and it’s interesting and it’s fun. Enjoy!Books:“Democracy for Realists,” by Chris Achen and Larry Bartels"Locking up our own,” by James Forman“Racecraft,” by Barbara Fields and Karen Fields"Ghettoside,” by Jill Leovy Learn more about your ad choices. Visit podcastchoices.com/adchoices

I have never come across a mind quite like Tyler Cowen’s. The George Mason economist, and Marginal Revolution blogger, has an interesting opinion on, well, everything. He’s a genuine polymath who can talk knowledgeably about more subjects than I even know exist.So coming in to this interview, I had a simple plan: ask Cowen for his thoughts on as many topics as possible. And I think it worked out pretty well. We discuss everything from New Jersey to high school sports to finding love to smoked trout to nootropics to Thomas Schelling to Ayn Rand to social media to speed reading strategies to happy relationships to the disadvantages of growing up in Manhattan. And believe me when I say that is a small sampling of the topics we cover. We also talk about Tyler’s new book, “The Complacent Class,” which argues, in true Cowenian fashion, that everything we think we know about the present is wrong, and far from being an age of rapid change and constant risk, we have become a cautious, even stagnant, society. This as information dense a discussion as I’ve hosted on this podcast. I took a lot away from it, and I think you will too. Books:-Autobiography of John Stuart Mills-Derek Parfitt’s Reasons and Persons-Fisher Black’s On Business Cycles  Learn more about your ad choices. Visit podcastchoices.com/adchoices

You may remember the Atlantic's Molly Ball from the fantastic pre-election conversation we had on this podcast. She's back this week to talk about an issue I've become more and more obsessed with — does factual argument matter in American politics? Or is it just a contest of identity activation?In the most recent Atlantic, Ball profiles Kellyanne Conway, whose television appearances and "alternative facts" offer an unusually clear window into this debate. We talk about that, as well as:- What's surprised us about Trump's presidency so far- How different elections activate different political identities- Fake news, how much it matters, and the ways in which it's rising among liberals- Why presidencies are defined by crises, and what we've learned about how Trump will manage his first- Whether Democrats are completely irrelevant now- How hatred of the other party became a more powerful motivator than belief in your party- Sean Trende's "missing white voters" theory- The low-grade espionage happening all over DC all of the time- Ezra's theory of what really happened between the Trump campaign and Russian operatives- Why Trump's approval numbers are far from disastrousAnd much more. Ball is one of my favorite people to talk politics with, and I hope you enjoy this conversation as much as I did.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

How do you actually run a White House? What is the president’s actual job? What is the chief of staff’s role? What happens if you screw up? These are questions I’ve been reflecting on rather a lot lately, for obvious reasons. And so I asked Denis McDonough on the podcast to talk about them.McDonough served as President Barack Obama’s chief of staff from 2013 to 2017 — a position in which he earned the nickname “Obama’s Obama.” This is his first lengthy interview since leaving the White House, and he was thoughtful, reflective, and sober about both the job he did, and the job his successors must do.This is a discussion about running the most important organization in the world well — and what happens when you fail. McDonough and the Obama administration did have their failures, and those failures taught them hard lessons.This discussion, to me, speaks to a great vulnerability opening up under the Trump White House. They are trying to pursue their agenda, but they are not effectively managing the vast organization they’re in charge of. That’s going to lead to mistakes, and those mistakes could come to define, or even destroy, this administration.Which is why, if there’s anyone who should listen to this podcast, it’s the current occupants of McDonough’s old workplace. This discussion is full of advice that’s useful to anyone running anything big, or anyone interested in how big things are run. I learned a lot from it. You will too.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

Before Cecile Richards was president of Planned Parenthood, she was a labor organizer working with garment workers in El Paso, Texas. The experience taught her a key principle of political change: people do things for their reasons, not your reasons.In this conversation, we talk about her organizing background, and how it's informing her work as she tries to protect her the institution she leads. Defunding Planned Parenthood is a core Republican promise. It is also, as she explains, a more punitive policy idea than people realize — there is no Planned Parenthood line in the federal budget, and so defunding the organization means denying it reimbursement for cancer screenings, birth control, and wellness visits. We dig into the possible consequences of that, as well as:-Why the core skill of organizing is listening-How she talks about Planned Parenthood with people who are pro-life-What today’s politicians could learn from her mother, Texas Governor Ann Richards-Why unplanned pregnancy and abortion rates are at post-Roe lows-The reason Planned Parenthood has tried to stop using the terms “pro-life” and “pro-choice”-What’s behind the sharp rise in IUD use-Why she thinks there’d be a very different debate over women’s health if more members of Congress could get pregnant-Which policies she thinks would work to drive down unplanned pregnancy in the US -What she thinks of Neil Gorsuch, Donald Trump’s nominee to the Supreme CourtAnd much more. Also, a quick programming note: we’re accepting applications for Vox’s next unconference, which will be held April 26-27th, and focus on the first 100 days of policy under Trump. Head to https://conversations.vox.com/events/spring-2017/ for more!Books:-Mountains Beyond Mountains by Tracy Kidder-Barbarian Days by William Finnegan Learn more about your ad choices. Visit podcastchoices.com/adchoices

Tim Ferriss is the author of the 4-Hour Workweek, as well as the new book, Tools of Titans. He’s also the host of The Tim Ferriss Show, which is one of my favorite podcasts, and an inspiration for this show. Tim is a relentless optimizer, and on his program, he interviews fascinating people to discover how they work, think, and get things done. It’s a show about the secrets of high performers. Here, I ask Tim about basically the reverse of that. How does he think about the parts of his life that, though crucial, are harder to optimize and systematize? We discuss friendship, love, psychedelics, spirituality, death, health, and whether it’s possible to get too addicted to productivity hacks. Amidst all that, we dig into:-Why Tim’s house is filled with reminders of his eventual death-Why he tries to build new friendships atop a foundation of shared suffering-Why he hasn't written a book on romantic relationships and probably won't-How productivity goes bad-How a serious bout of Lyme disease changed how he lives his life-Why some strange experiences on psychedelics convinced him there’s much more to this world than we understand-The difficulty of describing a sneeze-How his interviews have evolved since doing his podcast-What he feels constitutes good adviceOn his own show, Tim is always trying to offer takeaways and lessons about how to live, and he does that here, too. This episode is packed with ideas you can apply to your own life. Books:-David Deida’s The Way of the Superior Man-Frank Luntz’s Words That Work-Ted Chiang’s Stories of Your Life and Others-Peter Drucker’s The Effective Executive-Sebastian Junger’s Tribe-Oliver Sacks’ Gratitude-Less is More, an anthology on minimalist thinking-Ann Lamont’s Bird by Bird-Frank Herbert’s Dune-The Magic of Thinking Big by David Schwartz-Nikos Kazantzakis’ Zorba the Greek-Josh Waitzkin’s The Art of Learning Learn more about your ad choices. Visit podcastchoices.com/adchoices

Yuval Noah Harari’s first book, “Sapiens,” was an international sensation. The Israeli historian’s mind-bending tour through the trump of Homo sapiens is a favorite of, among others, Bill Gates, Mark Zuckerberg, and Barack Obama. His new book, Homo Deus, is about what comes next for humanity — and the threat our own intelligence and creative capacity poses to our future. And it, too, is fantastically interesting. I’ve wanted to talk to Harari since reading Sapiens. I’ve had one big question about him: what kind of mind creates a book like that? And now I know. A clear one.Virtually everything Harari says in this conversation in fascinating. But what I didn’t expect was how central his consistent practice of vipassana meditation — which includes a 60-day silent retreat each year — is to understanding the works of both history and futurism he produces. We talk about that, and also:-His theory on how all large-scale collaboration is based on fictions, from mythologies and religions to nationalism to human rights-Why he sees money as one of the greatest stories human beings have ever told-Why he reads only 5-10 pages of a huge number of books-His theory that human beings have moved from venerating gods, to venerating themselves, to venerating data — and what that means for our future-How we treat other animals and what that might imply for how artificial intelligences could treat us -Whether wide swaths of human beings will be rendered useless by advances in computing-The ways in which a narrow idea of what intelligence is — and the way it relates to consciousness — is holding us back from understanding AIThis is one of my favorite conversations we’ve had. Enjoy! Books:-Jared Diamond’s Guns, Germs, & Steel-Frans de Waal’s Chimpanzee Politics-Aldous Huxley’s Brave New World Learn more about your ad choices. Visit podcastchoices.com/adchoices

Elizabeth Drew is the author of Washington Journal, one of my favorite books about Watergate. Drew covered the story as a reporter for the New Yorker, and the book emerges from the real-time, journalistic diary she kept amidst the chaos. As such, it does something no other Watergate book does: tells the story not as a tidy tale with a clear beginning and inevitable end, but as an experience thick with confusion, rumors, alarm, and half-truths.Of late, I've heard a lot of people comparing the early days of Donald Trump's administration — with the strange scandals around Russia, the fast resignation of Trump's national Security Advisor, and the mounting pressure for investigation — with Watergate. And so I asked Drew, who is now a writer at the New York Review of Books, to provide some perspective on whether that comparison makes sense, and how to think about the Trump scandals that are unfolding, slowly and haltingly, right now.Books:-Philip Roth’s The Plot Against America-Andrew Schlesinger’s The Age of Jackson Learn more about your ad choices. Visit podcastchoices.com/adchoices

Avik Roy advised Mitt Romney’s 2012 campaign on health care, ran the policy shop on Rick Perry’s 2016 campaign, and then worked for Marco Rubio after Perry dropped out. So Roy’s Republican credentials are pretty solid. But he’s aghast at the direction his party has taken in recent years. The question Roy asks of conservatives today is a profound one: what is it you’re seeking to conserve? Under Donald Trump, he fears Republicans are fighting to conserve the idea of America as a fundamentally white, Christian country. “Trump showed me that white identity politics was the dominant force driving the Republican grass roots,” Roy told the Atlantic.Roy, who recently founded The Foundation for Research on Equal Opportunity, believes conservatism believes is bigger than that — and in this podcast, he explains why, even as he clearly details the difficulties the movement faces moving beyond white identity politics. We also go deep into healthcare, a subject Roy and I have been arguing about for years. A few other topics we cover:-What he thinks Trumpism represents as a phenomenon-How he feels he’s dealt with his identity as a conservative as opposed to as a Republican-How the aftermath of 9/11 led him to abandon a “colorblind” outlook on race-His hope for a new type of reform within the conservative movement that might result in  “diverso-cons”-How the innovator’s dilemma helps explain the GOP’s current problems-Why many conservatives don’t spend much time thinking about healthcare as an issue, and what they could learn from progressives who do-His thoughts on setting price controls for medical procedures and other costs to consumers-Why he thinks AI doctors might change medical practice and costs in the not-too-distant future-His criticism of how people on the left see nonprofit institutions as inherently more beneficial to society than for-profit companies, and the implications that has for healthcare-Whether Republicans are prepared to really offer an Obamacare replacement, and if so, what it might look likeBooks:-Leah Wright Rigueur’s The Loneliness of the Black Republican-Jonathan Haidt’s The Righteous Mind-Rationalism & Politics and Other Essays by Michael Oakeshott  Learn more about your ad choices. Visit podcastchoices.com/adchoices

Before I launched this podcast, I asked Kara Swisher to coffee. Swisher founded the technology news site Recode, hosts the excellent Recode Decode podcast, and runs a legendary conference series. She is among the best interviewers working today. Some of her gets — including the first and only dual interview of Steve Jobs and Bill Gates — have passed nearly into myth. I've used the advice Swisher gave me in every episode of this podcast. But in this conversation, she goes further, offering her tips both for interviewing and reporting. If you want to be a journalist, or you just want to talk to people, you should listen to this. Swisher is also an excellent, hilarious storyteller who has lived an incredible, strange life. You really, really don't want to miss the story of how she became part of a sexual harassment lawsuit against John McLaughlin, and why he thanked her for stabbing him "in the front." You also don't want to miss:-The alternative life she might have led as a CIA analyst-Why she thinks journalism school is a waste of time and what she advises people to do instead-The importance of staying in touch with sources when you're not writing about them-Her thoughts on relative friendliness of reporters and sources on politics versus tech beats-Her advice about interviewing -Why she wants to run for mayor of San Francisco, and what she'd want to do as mayor-What aspects of Trump appeal to her-Why she thinks social media’s bad for the world and probably won’t get betterThis is one of the funnest conversations I've had on this podcast, and it's also perhaps the most useful. Enjoy it. Books:-The Woman at the Washington Zoo by Marjorie Williams-Barbarians at the Gate by John Helyar and Bryan Burrough-Alexander Hamilton by Ron Chernow-Jhumpa Lahiri’s Interpreter of Maladies-The audiobook of Hilbilly Elegy by JD Vance -Megyn Kelly’s Settle For More-Atul Gawande’s Being Mortal-When Air Becomes Breath by Paul Kalanithi-A Wrinkle In Time by Madeleine L’Engel-The Time Machine by Jules Verne-Are You My Mother? by Alison Bechdel-Time and Again by Jack Finney Learn more about your ad choices. Visit podcastchoices.com/adchoices