How Politico’s Next Generation Took Over Washington – Vanity Fair

It’s been a year since Anna Palmer, Jake Sherman, and Daniel Lippman took over Politico’s Playbook newsletter, the always insightful, relentlessly insidery bible for Washington’s swamp-creature class. They faced a tough job, stepping in for the indefatigable Mike Allen, who created and oversaw Playbook with an intensity and flair that felt hard to match. Lippman had helped Allen with his column since 2014, but he took over full-time with Palmer and Sherman one year ago, on July 11, 2016. Since then, the three have crisscrossed the country, launched a podcast, an afternoon newsletter, and thrown themselves into the event business. They also just sold a book about the backroom deals and dramas on Capitol Hill, scheduled for release after the 2018 midterm elections, provisionally titled “A Hill to Die On.” We caught up with Palmer and Sherman—Lippman was on the road, as he often is—as they prepared to celebrate their first anniversary running Playbook. Here, they talk about how to make friends in Washington, what it’s like covering the Trump White House, and why politics is the most fascinating story on earth.

The Hive: Happy Birthday!

Sherman: Do I get a gift for this?

So, just to get this out of the way: Anyone following a big name inevitably faces comparisons with one’s predecessor. How was it to follow someone like Mike Allen?

Sherman: We were both very close colleagues with Mike, who was a mentor of ours, and he encouraged us to do this at the outset. The way we oriented our thinking back in 2016, we weren’t going to try to be Mike Allen. We aren’t Mike Allen. We are Jake and Anna and Daniel. But people did like what they were doing with Playbook.

Palmer: Mike created the Washington newsletter and deserves a ton of credit. We approached it as a second generation relaunch of a brand.

What was your strategy?

Sherman: We have readers in all 50 states, and we see Playbook as the connective tissue, not just for people in Washington involved in the political game but for people in San Francisco, Los Angeles, and Chicago, who are involved, interested, or need to understand it to conduct their daily business.

We’ve done it in a more purposeful and methodical way not just through events but also by building out a source network. It’s what we try to think of as constituent service. The Playbook community is all over the country. All these additions have been wildly successful. More people are reading Playbook than ever before and more people are opening it than ever before and it’s making more money than ever before.

Do you have numbers you could share with me?

Sherman: Subscriber numbers are up 35 percent. And we do routine list maintenance. People in D.C. are transient. We clean out the list of dead addresses, and we’ve had tremendous growth even with that.

Palmer: We’ve been focused on people who are new in town. We are also focusing on businesses, the C-suite, companies and business people affected by politics. Every Senate office and every House office has a subscription.

Sherman: And obviously, the White House. They’re all reading it.

How do you know who is reading you?

Sherman: They have to fill out information to get the newsletter. And they are easily Google-able. And believe it or not, people feel very open and willing and able to talk about Playbook and the news. We build many personal relationships with many of our readers.

And they are opening up the newsletter more?

Sherman: Open rates are 10 percent higher than they were ever before. [He declined to provide underlying numbers, saying not to was “our blood oath.”] We track it as does every newsletter. It’s a crucial metric. It’s a nice ego boost.

You mentioned out-of-towners. That would include a lot of people in this White House. What is it like covering this White House versus the Obama White House?

Sherman: A lot of the newcomers have pretty traditional D.C. hands working for them.

Palmer: Clearly, Donald Trump’s White House doesn’t have the same kind of messaging strategy that’s been typical of Barack Obama in terms of setting the message for the day or the week. Trump’s use of Twitter changes how we cover official communications from the president.

Sherman: If the president chooses to communicate through Twitter, we can’t just say we aren’t going to cover that because of the medium he chooses. Our goal is to prepare our readers going into their day. So they know the latest news going into their 8 A.M. meeting and are smart.

Palmer: We try to synthesize what is important for our readers. We try to decipher what he’s communicating—to deliver that perspective.

Sherman: We also think it is one of our duties, when an administration official says something, that we give the context of what it will mean in the larger political situation. When they say we will do tax reform by August, there are certain political realities where we add value.

What’s been your biggest scoop? The story you are most proud of?

Sherman: We are doing things twice a day now. We don’t keep a running list, unfortunately, we probably should! And it’s a lot of momentary stuff. Like, “Here’s what is going to happen today.”

Palmer: One memorable thing we’ve done is to create the Playbook Interview, which has been a way to interview high-level people on the news when people want to send a signal to Washington, like Warren Buffet or Bill Gates. That’s an area where we’ve been able to drive the news cycle.

What’s coming in Year 2?

Sherman: The one big thing is we are writing a book, and we are excited about that. We are doing it because we think Congress is one of the best stories in Washington. The back story to that is always fascinating. We talked to people at C.A.A. [Creative Artists Agency] about that and they said, “Wow, we like that book too.” So we are doing it with Crown and it is coming out in March 2019.

Palmer: We are a backbone of a big franchise. We are in six states. We have launched a Brussels Playbook and we are launching a London Playbook. We are looking to internationalize the brand , and you’ll see more focus on that.

With all of that going on, when are you going to find time to write a book?

Sherman: We have 28 hours in our day. We have a special dispensation. No seriously, we are working on that now and we’ve been working together since 2010, and this is a book we’ve been writing in many ways since 2010. Our goal is the bring our readers into the rooms they can’t get into and tell them the inside story of how Washington works, or doesn’t work. It is a Capitol Hill book. It isn’t a Donald Trump book.

Palmer: The book starts the day after Election Day in 2016 and runs until the day after the election in 2018. The first two years of any administration are critical. The second two years are often consumed by a political election. There is a lot happening behind the scenes. We think the Hill is more important than ever before. It’s gained more relevance than ever before.

It certainly seems relevant now in terms of the health-care bill. What’s your thought on how that will play out?

Palmer: We really try not to be in the prediction business, to predict what is going to happen in this environment. We like to cover every turn of the screw.

Sherman: What we said this morning is that it’s a really, really narrow line they have to walk getting this thing through. We try to cover the political realities, not just what the administration says. It’s always been a tough road to repeal and replace this thing on the time frame the Trump administration outlined.

I heard the working title is “A Hill to Die On.”

Sherman: The truth is, we haven’t figured it out yet. We wrote a proposal and we’ll figure it out as we go.

Palmer: It depends on where the story goes. We’ve discussed that title, but we have discussed others as well.

Who have you identified as your main characters?

Sherman: We can’t tell you. There are certain big figures on the Hill who will definitely be in the book. We are looking at who they are and what drives them and how they comport themselves. It’s politics as pop culture. But it is also a book about people and relationships, feuds and friendships, and building alliances and all the things that make politics the most fascinating story. It’s not the future of the Republican Party.

John Kerry after the Democratic National Convention at the University of Massachusetts Boston, on July 29, 2004.

John Kerry after the Democratic National Convention at the University of Massachusetts Boston, on July 29, 2004.

Kerry after an event in Jefferson City, Missouri, on August 5, 2004, during a “Believe in America” tour.

Kerry after an event in Jefferson City, Missouri, on August 5, 2004, during a “Believe in America” tour.

Hillary Clinton leaving an event in Cedar Rapids, Iowa, in July 2007.

Hillary Clinton leaving an event in Cedar Rapids, Iowa, in July 2007.

John Edwards at the Iowa State Fair in Des Moines, Iowa, on August 16, 2007.

John Edwards at the Iowa State Fair in Des Moines, Iowa, on August 16, 2007.

Barack Obama during a Democratic debate at St. Anselm College in Manchester, New Hampshire, on January 5, 2008.

Barack Obama during a Democratic debate at St. Anselm College in Manchester, New Hampshire, on January 5, 2008.

On the street waiting for a candidate to show up in Concord, New Hampshire, in January 2008.

On the street waiting for a candidate to show up in Concord, New Hampshire, in January 2008.

Bob Dole leaving an event in Green Bay, Wisconsin, in October 1996.

Bob Dole leaving an event in Green Bay, Wisconsin, in October 1996.

Jesse Jackson at an event at the black-history museum in Greenville, South Carolina, 1987.

Jesse Jackson at an event at the black-history museum in Greenville, South Carolina, 1987.

Al Gore, Gary Hart, Michael Dukakis, and Jackson after a Democratic debate, before Super Tuesday in 1988.

Al Gore, Gary Hart, Michael Dukakis, and Jackson after a Democratic debate, before Super Tuesday in 1988.

Dole at an event in Louisiana, 1996.

Dole at an event in Louisiana, 1996.

Before a Pat Robertson victory party on Super Tuesday, March 8, 1988, in Atlanta, Georgia.

Before a Pat Robertson victory party on Super Tuesday, March 8, 1988, in Atlanta, Georgia.

George W. Bush leaving a press conference in Iowa, in 2000.

George W. Bush leaving a press conference in Iowa, in 2000.

A pro-Bush rally outside the Texas Capitol in Austin, Texas, in November 2000.

A pro-Bush rally outside the Texas Capitol in Austin, Texas, in November 2000.

Dennis Kucinich supporters before a Democratic debate in Durham, New Hampshire, on December 9, 2003.

Dennis Kucinich supporters before a Democratic debate in Durham, New Hampshire, on December 9, 2003.

George H.W. Bush during the general election in Omaha, Nebraska, on October 28, 1988.

George H.W. Bush during the general election in Omaha, Nebraska, on October 28, 1988.

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