The offices of Crooked Media occupy a suite on the fifth floor of a modern but unassuming building in Hollywood, California. The front door opens onto a neon rendering of George Washington wearing earbuds, the physical embodiment of Pod Save America’s bright yellow logo, set against wallpaper reproducing political headlines through the decades. With its Edison bulbs, concrete floor and unfinished ceiling, the chic open-plan space could be the headquarters of any tech startup. Its identity as the home of “the voices in blue America’s head” (as the New York Times Magazine put it) is only revealed by the Pete Souza photo books decorating the coffee table.

Tommy Vietor ’02, dressed SoCal casual in a T-shirt and khakis, emerges from a meeting in the large, glass-walled Collusion Room. (At Crooked Media — a tongue-in-cheek moniker that references President Trump’s nickname for news organizations that are critical of him — the conference rooms are named after crimes the administration has been accused of committing.) After a brief tour of the two podcasting studios at the heart of the company’s burgeoning empire, Vietor escorts me into the cozy Fraud Room, where his energetic chocolate labradoodle, Lucca, cozies up to him on the couch.

Part I: Finding his philosophical footing

“I wish I had a good answer,” Vietor said when I asked him why he’d chosen to leave his hometown of Boston and head to college in Ohio. When he moved into McBride in the fall of 1998, Vietor was following in the footsteps of his older brother, John Cunningham ’95, and a cousin, Jeremy Button ’95. “I visited and I loved the campus — you know, when you visit Kenyon in the spring or early fall, it’s the most beautiful place on the planet,” he said, adding, “They don’t tell you about the February days.”

He initially assumed he would major in English, but found himself drawn to philosophy — a calling that surprised Professor Juan De Pascuale, who taught a first-year Vietor in the introductory course “Philosophy of Religion.”

“He did rather poorly in that class. I thought I’d never see him again,” recalled De Pascuale. “What’s impressive is that someone who did so poorly in ‘Philosophy of Religion’ would probably have avoided that professor, but he showed up next semester in my existentialism class.

“And it was maybe a different Tommy,” De Pascuale continued. “What emerged in that course was an earnestness, I would say, and maybe also a certain kind of intensity.”

Vietor quickly found a home in the philosophy department, going on to study Nietzsche with De Pascuale and logic with Professor Andrew Pessin, who now teaches at Connecticut College.

“I loved the luxury of being 21 or 22, and pondering the big questions about existence and why we’re here, and all the shit you do in a philosophy seminar from 7 to 10 p.m. on a Tuesday,” Vietor explained.

Pessin recalled Vietor, who was one of his academic advisees, as being “super smart, with lots of ideas.” Still, “I remember thinking that he did not always work up to his full potential,” Pessin said. “He carried himself with a very appealing degree of self-confidence that indicated he was probably going to go far.”

Looking at his later career, it might come as a surprise that Vietor didn’t focus on politics or public policy in Gambier. But, especially considering the political science department’s historical emphasis on theory and philosophy, Vietor viewed the disciplines as two sides of the same coin.

“It’s like, same books, different chapters, you know?” he said.

The intensity that De Pascuale identified, along with Vietor’s self-identified “fleeting attention span,” also found an outlet on the lacrosse field. “I wasn’t a great athlete,” he acknowledged. “But it was a chance to, instead of waking up in the morning and going to a gym and slogging it out on a treadmill and being miserable, you get to go run around on a field with your best friends for two hours every day.”

Those friends — many of whom attended Vietor’s wedding to marketing executive Hanna Koch in the summer of 2018 — were foundational for Vietor.

“The friendships and relationships that formed who I am as a human being were people I met at Kenyon,” he said. “You become who you are because of the people around you, and Kenyon’s great in fostering that environment. I always think the value of Kenyon is the people, and the intimacy of those friendships.”

Part II:  Path to the White House

Beyond familial discussion of current events, Vietor did not grow up with a passion for politics. “I would not say I was particularly politically engaged or active at Kenyon,” he said. “When I graduated from college, I wasn’t sure what to do.”

Back at home in Massachusetts, a bit of luck and a serendipitous family connection helped Vietor land an interview with the office of then-Senator Ted Kennedy, which led to a summer internship. Working for the liberal lion of the Senate is what made Vietor realize politics was “something I really care about and want to do.”

“Ted Kennedy, for all his faults, was a guy who woke up every day and literally would go down to the Senate floor and shout for the things he cared about,” he said. “It was hard not to be inspired by him, and who he was, and all the things he did. So that’s where I really got the bug.”

Finding a full-time position in Washington, D.C., proved difficult after, Vietor says, “Democrats got their asses kicked in the 2002 midterms,” but eventually Vietor got a job with the presidential campaign of John Edwards — “before he was a total creep,” Vietor hastened to add, referring to the former North Carolina senator’s extramarital affair and federal indictment.

Once Senator John Kerry became the party’s apparent nominee, Vietor’s career took an unexpected turn. The former intern for Massachusetts’ senior senator could have joined the state’s junior senator’s presidential campaign — but instead he headed to Illinois, joining a rookie politician on what would ultimately prove to be a surer path to the White House.

In the summer of 2004, Barack Obama was a little-known state senator embarking on his first run for federal office. “I started reading everything about him, and I read his book [‘Dreams From My Father’], and I just got completely obsessed with wanting to work for him,” Vietor said. “So I emailed David Axelrod and Robert Gibbs, as often as I thought wasn’t stalkerish, until I got hired. I got the call, and six days later I was gone.”

As deputy press secretary for the campaign, Vietor juggled writing press releases and op-eds, staffing interviews and talking to reporters. But like many campaign staffers, he also jumped in wherever needed, sometimes handling logistics for the press corps — leading some critics to refer to Vietor as a mere van driver and question his qualifications for his role in the White House. “That happens on every campaign — you do every job, big or small,” Vietor said. It was while doing one of those small jobs Vietor first met the man who would be his boss for the next decade.

“I was in the office late one night and I had printed out a bunch of press packets, and I had screwed up when I did it,” he remembered. “I was having to sort and reassemble everything; I had my shoes off because the air conditioning went off and it was just baking in the office. And then he walked in.

“So the first time I met him, I was sitting barefoot on the floor in a ratty T-shirt, sweating my ass off. I think I shook his hand and stared at him with my mouth open and then he went on to do whatever he had to do. And I felt like, ‘Oh great, that was not the best introduction.’ You obsess about the moment when you’re finally going to meet this person who inspired you so much. Everyone has some dumb fantasy where they do something that saves the day and then meet the candidate, and your value is clearly evident to them right from that moment. But it’s always a little more humbling than that.”

After the election, Vietor became Obama’s primary Senate press secretary, and, in 2007, when Obama announced his longshot bid for the presidency, the campaign’s Iowa press secretary.

Despite being a relative newcomer, Vietor picked up on the media job quickly. “A liberal arts degree and a press secretary job are similar,” he said. “You’re learning a lot about a whole bunch of different things, and you don’t have to master it, you’re not getting your Ph.D. in whatever issue you’re talking about that day, but you need to really know your stuff to be able to succeed.”

Part III: Crash course in foreign policy

Once the Obama campaign transitioned to the Obama administration, Vietor faced the unglamorous reality of governance: moving into a cramped office as one of the new president’s press aides. Despite the small size of the staff, Vietor at one point found himself sharing the West Wing basement with two fellow Kenyon alumni, deputy press secretary Jamie Smith ’99 and press assistant Jesse Lewin ’07.

Lewin, who now works in corporate communications for McDonald’s and counts himself among Crooked Media’s many listeners, agreed with Vietor’s description of the tight space. “We could swivel around our chairs and give high fives,” he said.

As an assistant press secretary during the first half of Obama’s first term, Vietor’s job was to help the White House press corps tackle issues regarding education, labor, the State Department and the Department of Defense. Over time, his role became primarily focused on national security. From January 2011 until he left the White House in March 2013, Vietor served as spokesman for the National Security Council.

Through it all, Vietor developed his specialization in foreign policy, learning as he went. “By osmosis, and being in meetings, and talking to smart people and being on trips, I realized how interesting and important those decisions were, and how consequential they were,” he said. “It was like a grad school education while I did my job.”

One of the most memorable days was May 1, 2011. After the previous night’s White House Correspondents’ Dinner, Vietor had been “out as late as I’m ever out in my life” and the following day was summoned urgently to the Situation Room. “I asked what was going on, and one of the guys I worked with threw a photo down on a table,” Vietor recalls. “It was the photo of bin Laden with a bullet in his head.”

After the president disclosed the al-Qaida leader’s death late on Sunday night — “There were some people debating whether we should make an announcement, and [Deputy National Security Advisor] Ben [Rhodes] and I were like, ‘Guys, you just parked a f**king helicopter in some guy’s backyard in Abbottabad, there’s not a choice here.’” — Vietor walked home from the White House, through a large crowd that had assembled outside.

“They were chanting, ‘USA, USA,’ and it was this weird, very surreal moment,” he said. For Vietor, who was a senior at Kenyon on 9/11, and who learned of the attacks during his 9:40 a.m. “Introduction to Computer Science” class, “it was an incredible day.”

Although he claims never to miss “the trappings of the West Wing” — “I didn’t have a window, there’s mold, there are rodents” — Vietor couldn’t help but recall the sense of awe inherent to the building. “The times you end up giving people tours are the best, because you see it again through their eyes,” he recalled. “You realize that there’s a sense of stillness in the air, and you walk into the Oval Office. You don’t really know why — it’s just a room — but there’s so much history there, and it feels … it’s an amazing, emotional thing.”

Part IV: After the Oval Office

By the time Obama began his second term in 2013, Vietor was burning out. “Two years on a presidential campaign, four years in the White House, that is six brutal work years,” he said.
“Six years of working at least one day a weekend, eating three meals a day at a desk. And I was just exhausted and done with it.”

Still, going cold turkey on the adrenaline rush of the West Wing was a difficult transition. “I wasn’t emotionally prepared for how quickly you are no longer in the mix with that same group of people,” Vietor said. “If you think of the White House as a motorcade that is just going all the time, if you’re not in the motorcade, you’re left behind. The minute you jump out to stop working there, they race off without you.”

Plus, “my best friends all worked there,” he said. “You forge this pretty intense relationship because you’re dealing with adversity together, trying to figure out a problem, and you literally can’t talk to them about that stuff anymore.

“The times I went back [to the White House] to visit or to see people for work reasons, it was weird. It was kind of the equivalent of, if two years after college I went back and saw my old dorm room, and it was a place I knew, and it used to be mine, and I loved it, but it wasn’t my home anymore.”

Tired of watching the action from the sidelines in D.C., Vietor moved to San Francisco in search of a fresh start. Obama’s director of speechwriting, Jon Favreau, left the White House at the same time and moved to Los Angeles. Together, the two Boston natives founded a communications consulting firm called Fenway Strategies.

“I got to work with great people, and do some cool writing, but ultimately I was working from home in San Francisco and it was just lonely,” Vietor said. One thing hadn’t changed since Vietor’s days playing lacrosse for the Lords — he wanted to be part of a team.

Part V: “Pod Save the World”

Vietor’s first podcasting gig was co-hosting a show, “Keepin’ it 1600,” on the sports and pop culture network The Ringer, alongside Favreau and fellow Obama alumni Jon Lovett and Dan Pfeifer. But the show, which debuted during the heated 2016 Democratic primary season, was not concerned with activism. Like many others, Vietor and his buddies assumed that Hillary Clinton’s small but consistent lead in polls would ensure her victory, leading them to over-confidently caution against the political “bedwetting” of those who feared a Trump victory.

But then, “the election happened, and we were all despondent,” Vietor said. “And also, I think, guilt-wracked, because we sure as hell didn’t do anything to change the outcome.”

The trio of Vietor, Favreau and Lovett transformed their venture, almost overnight, into a new show whose title reflected what they perceived as the country’s dire circumstances: “Pod Save America.” Frustrated by how the election had been covered by mainstream and right-wing media, the three saw a need for an activist liberal counterbalance.

“Breitbart can make something up and then Fox can run it, and then the whole press corps has to talk about it because it’s in the news,” Vietor said. “We don’t want to be dishonest, we don’t want to be scaring people or peddling hate, but we want to find a way to create stories about things we care about,” he said, with the goal of becoming “a big important platform for progressives to talk about progressive ideas.”

It turned out to be a winning formula. According to Vietor, about two million people download each episode of “Pod Save America,” which is released twice a week. Up to 800,000 people on average also download Vietor’s weekly foreign policy-focused show, “Pod Save the World.” The pod bros, as they’re sometimes known, receive rock-star welcomes from sellout crowds at live recordings across America, have appeared multiple times on “The Late Show with Stephen Colbert”, and adapted their flagship podcast into a series of TV specials for HBO in the run-up to the 2018 midterms.

Despite Vietor and his pals being the most visible faces of Crooked Media, “It can’t just be three white guys of the same age who all worked for Obama,” Vietor said. “Our goal was, from the very beginning, to find hosts and create shows with them in partnership.”

The fact that I can get a million people to download a podcast about a bunch of foreign policy issues is mind-boggling to me.

Tommy Vietor, on his podcast "Pod Save the World"

Although Vietor gets his “political fix” as one of the co-hosts of “Pod Save America,” his real passion project is “Pod Save the World.” During his time in the White House, whenever a reporter called Vietor about a world event, he would “call the NSC [National Security Council] person who was the expert on it, literally patch them through, hit mute and listen. And then I would learn as much as they would.

“‘Pod Save the World’ is recreating that phone call, trying to bring people into the room and demystify complicated things,” Vietor said. “The fact that I can get a million people to download a podcast about a bunch of foreign policy issues is mind-boggling to me. And I love it.”

Vietor sees “Pod Save the World” as a way to give others the same crash course he received early in his career. “I want people to understand that these big decisions are not things they should ignore and let others decide,” he explained. “If you care about this stuff, get yourself informed, and think about joining the foreign service or the intelligence community. You can do these jobs. You can be a part of this stuff.”

Take a moment and imagine that Crooked Media succeeds in its mission of informing and galvanizing a progressive movement, and, on Jan. 20, 2021, a new occupant of the White House is looking to build a staff. Would Vietor want to be a part of the action again?

“Go back in? I don’t think I would go back in,” Vietor said.

“I mean, never say never.”