Someone once told me that if you do what you do well enough, eventually, you’re going to end up in Washington D.C. It’s inevitable. The nation’s capital has some of the greatest minds this country has to offer. Every summer and fall this city is filled with new young minds ready to be molded into tomorrow’s lobbyists, civil rights attorneys, or nonprofit organizers. However, this town will always and forever more be connected to politics and the people who shape the conversations around it. Tim Russert, Wolf Blizter, Woodward & Bernstein, the list goes on and on. If politicians were a great outfit then the journalists who report on them are the shoes and accessories that bring the whole look together. They provide balance to the political landscape by keeping the people in power honest and providing a voice for citizens who have questions that need answers. “House of Cards” is a great show and all (Rest in Peace to Zoe Barnes) but this is real life and you need real people to cover it. Enter Anna Palmer and Jake Sherman.
On July 11, 2016, Anna and Jake took over the day to day operations of Politico magazine’s flagship product, Playbook. The daily newsletter is a must-read briefing for anybody who considers themselves in the loop in and around the beltway. It was operated by Mike Allen, a chief political reporter for Politico, for over 10 years before he stepped down earlier this year. Anna is a native of North Dakota and St. Olaf College graduate. Jake hails from Connecticut and was one of those young minds the city welcomed at George Washington before he attended Columbia University’s Graduate School of Journalism. Both of them bring a wealth of political reporting experience to the table prior to this role. Together they look to carry the torch for Playbook into a new era.
DCLM: How does the vetting process for something like taking over Playbook go?
Jake: Funny we always said it’s like the TODAY show you can’t switch out the cast that easily! LOL. Early on when Mike said he was leaving our owner says “How do you replace a one man army you get an army” I’ve been at Politico for 7 years, Anna for 5 so it was a natural progression. We grew up here professionally so this was naturally the next step rather than leave and take our game somewhere else we wanted to grow Playbook and see what we could turn it into.
Anna: I think it was a decision that took many months. When Mike decided to leave the company there was a decision made that we either end Playbook with his departure or we continue it. Second acts are always hard. There were months of memos and meetings that took place centered on how we would move forward and how we would innovate. Keep the heart of what Playbook is and always put our own stamp on it.
DCLM: Is this something that you always coveted?
Anna: I don’t think this was something that we anticipated would ever happen. When it did I think we looked around and realized this was something you couldn’t pass up. To be around the best political journalism news product that sets the political agenda every day.
DCLM: What is the motivation to take over and make this newsletter your own?
Jake: It’s a unique product and we found more out of it when we took it over. People wake up to it as they have for the last 10 years. We looked at this kind of like growing up in the Bronx and wanting to play for the Yankees. We don’t want to be Mike Allen. Nobody is going to be successful that way. We thought we embodied the spirit of Politico and what Mike brought to the table with Playbook. We have different frames of reference. We came of age professionally in the era of Barack Obama. That lends itself to a whole new set of characters added onto to the players that Mike was associated with.
DCLM: How does the constantly changing political landscape affect the way you cover the day to day stories?
Jake: I think the one constant is that people still want to break news in Playbook. There are people in Los Angeles, Chicago, D.C., and San Francisco that still rely on Playbook to break news. We are pretty fortunate that Politico is a news organization that is pretty set in stone whether we are covering the Trump campaign or the Clinton campaign or a story centered on cyber security.
DCLM: What is a typical day for you?
Anna: I don’t know if there really is a typical day. We are at work by 4 a.m. There are lots of things that go into the job. Events and meetings that shape a story we are working on. Most recently with the conventions, we were in Cleveland and Philly just covering everything that was going on. I think what Jake and I have found so far is that every day is just so different.
DCLM: Has anything surprised you so far since taking over?
Anna: I think what has really been surprising and very heartening as well is that people genuinely want to help and be helpful. We recently started a new feature called Playbook interview which is a way to get newsmakers to help build buzz around the product and we’ve had people come to us whether it be CEOs, thought leaders, politicians and told them if you want to send out a signal or message to Washington this is the place to do it and they have been very receptive whether it’s been Warren Buffett or Stephen Colbert or General David Petraeus.
Jake: For me, the biggest surprise has been how receptive the audience has been. Going into taking over something like this you’re worried about things like, “Will I be able to keep the subscribers? Will I be able to keep the intensity? Not only have we retained the original audience but we are bringing on new subscribers at an extremely rapid rate.
DCLM: How has the changing landscape of journalism affected a scoop heavy newsletter like Playbook in your eyes?
Anna: We obviously come in this with a journalism background. That’s what we are first and foremost. So I think we bring a code of ethics on how we treat sources the same way we would have in covering stories when we did on The Hill or anywhere else.
Jake: We always make sure our integrity is kept intact. That means if a person wants to speak with no attribution that’s fine but we would never allow for an “anonymous source” to trash anybody else in our newsletter. There really is no room for that in what we are trying to offer.
DCLM: What are essentials for you? Things you’ve found you need to do this job?
Jake: Exercise! If I don’t do my 50 minutes of exercise a day you don’t want to be anywhere near me. I’m actually going to go after this interview LOL.
Anna: I can confirm that is true for Jake LOL. For me its coffee, Gchat, and Daniel Lippmann. He is essential to what we do every day. He worked with Mike and he sees things we don’t see and knows people we don’t know. He works really hard. He brings another layer to this whole thing that is absolutely must have.
DCLM: Do you feel pressure to uphold not only playbook but Politico as well?
Anna: I think we both understand the responsibility we hold not only externally, that we present the best product that we can every day and how we present and conduct ourselves around town by representing the product and the company to the best of our ability, but internally as well. We have an obligation as top reporters to do everything we can to make sure that this is a great place to work. That means being helpful as colleagues and making sure that we are engaged in the work all the time.
Jake: I think there is this huge pressure in imagining that every morning people are going to wake up, roll over, grab their iPhone and read Playbook. So you want to be fair and even because people feel an intimacy with the product and they’re going to let you know how you’re doing. To take another baseball analogy, if we’re not calling balls and strikes then that’s a problem and they will let you know. So you want to be honest and open and fair and even and do all of that between the hours of 4 – 7 a.m. So that’s a challenge and it’s tough and daunting but fun at the same time.
DCLM: What new features are you going to be bringing to Playbook?
Anna: The first couple months we really focused on making sure the newsletter was done right and making sure we crafted a voice and got that squared away. The next iteration will be Playbook Plus. It will be launching in September, and it’s basically all the best parts of Playbook. The heart and soul kind of broken out into different items that are beyond the newsletter. We’ve started a 90-second audio flash briefing of the best of playbook every day that can be downloaded for people to listen to on the train or getting ready for work. There will be a feed from our Twitter and Instagram accounts.
Jake: One of our big pitches is making it a more wholesome product outside of the newsletter that reaches everywhere our readers are. That includes Snapchat, Facebook, Twitter etc.
DCLM: What type of mantras do you live by?
Anna: There is no substitute for excellence.
Jake: Be essential and indispensable.
DCLM: What type of advice would you give to anybody trying to follow in your footsteps?
Jake: You need to be indispensable in one area. Your employer needs to know that you are the go-to person on a particular thing whether that be on the White House or technology or Capitol Hill.
Anna: I think getting experience early on is so vital. Finding out what you don’t want to do is just as important as finding what you do want to do. No job is too small for you. Helping people along their journey is just as important in getting an opportunity. I held a number of jobs prior to breaking into journalism and it just gives you a greater appreciation knowing that the work you contribute, big or small, matters to whatever organization you are working for.
DCLM: Ultimately, what do you see your legacy like with Playbook 10, 15, 20 years down the road?
Anna: We would like to institutionalize what was the organic growth of a personal email that was monetized into an actual franchise. My goals would be that someday it won’t be the Jake and Anna show and whoever carries it next, that we have set the foundation for them to carry it into perpetuity as the must-read for Washington.
Jake: Success is the keyword for me. We want to take this thing to the next level. We want to find however may people in power centers around the globe who aren’t reading Playbook and get them to start reading it. We want to grow. We want to make this a business. Its’ already a business within a business but we want to make it an empire. Playbook is the connective tissue of all the big power centers in the country. Everybody in those centers reads it because they want to know what Washington thinks. This is bigger than us. This was bigger than Mike. Think of how many things like this are still successful after 10 years. Things have a shelf life. It goes beyond one person. Hopefully, there will be life after us but we aren’t anywhere close to that yet.