Where are you from, and what brought you to Rome?

I am from different places in New York state; I was born in the city, grew up in the suburbs, and later moved to a rural part of Upstate New York. What brought me to Rome is a bit of an odd story. I found the school on Google. I was an imaginative child, and my dad and stepmother were getting a divorce, and I wanted to escape, so my imagination led me to search for boarding schools in all different kinds of places.

I was 16, but my dad told me if you apply and visit, and do it all on your own and prove to us that you’re grown up enough to do this, then you can do it. I visited St. Stephen’s by myself, I got in, decided to go, and it was one of the best decisions of my life.

Why was it one of the best decisions?

Coming from a rural town in Upstate New York, attending St. Stephen’s allowed me to grow up, have different experiences, and meet all kinds of people before going to college. Because of St. Stephen’s, the process of growing into myself and feeling more confident, more like an adult, had already begun before I got to college.

For most people, freshman year is a time of experimentation and trying new things, trying to figure out who you are when you are no longer tethered to your parents, and I felt like I had already started that process.

What are some of your fondest memories of being at St. Stephen’s?

There are a lot [of memories]; I loved my time at St. Stephen’s. First and foremost: the community feels like a family; people are friends across all grades; as a senior, some of my best friends were sophomores, and they are still my close friends today. It’s a place that immediately felt like home even though I’m not Italian, had never lived in boarding, had never even attended a private school, [but] it felt comfortable right away.

For spring trips, I went to Jordan, a trip led by Lesley Murphy, my favorite teacher. We slept in the Wadi Rum desert, gazed at the stars, and danced to Jordanian music; it was a cool experience.

To my point about Lesley Murphy being my favorite teacher, I had her as an English teacher, and that was my favorite class; she was one of the first people in my life who said you’re a good writer and you should pursue this--which is adjacent to what I ended up doing in my life. Having somebody tell you that and have confidence in you while you’re doing school work, that is meaningful and [created] this incredible relationship which meant a lot to me. [Lesley] encouraged everyone to have different perspectives, take risks in their writing and do unique writing projects. And it goes back to having confidence in myself by the time I started college.

After St. Stephen’s, what came next?

I went to Johns Hopkins University [for undergrad]. I was interested in international studies--which was part of the reason I went to Rome in the first place--, and that continued to be the case throughout college. I majored in international studies, and I ended up double majoring in Italian studies. I returned to Rome the first two summers of college; the first summer, I did an internship at the World Food Program, and the second summer, I studied at La Sapienza. Both summers, I stayed with former St. Stephen’s students. So, although I left Rome, St. Stephen’s continued to have an impact on my studies and my friendships (and it still does to this day). I started off wanting to be a diplomat and ultimately decided that was not for me, but I didn’t know what I wanted to do. So I iterated, tried different things, thought of pursuing academia, and finally ended up interning for the local NPR affiliate in Baltimore. I liked it enough to decide to try it.

So, did you continue at NPR after that first internship?

Not exactly. I didn’t have a full-time job for almost a year after I graduated. I decided that I wanted to be a journalist in 2012, and that was a difficult market to break into; it still is, particularly in the audio world. In 2012, podcasts had not [yet] taken off, and public radio and NPR specifically were historically places where you have to wait forever to get the job you want because there are so few jobs and so many people trying to do them.

I moved back to New York City without a job. I moved in with the parent of one of my classmates from St. Stephen’s, an empty nester who told me when you graduate from college, if you don’t have a job lined up, come and stay with me and you can figure it out here in New York City, it’s the best place to discover how to chart your life forward. I ended up interning and freelancing at WNYC, the NPR affiliate, and applying to probably hundreds of jobs and, most of the time, failing. One day, my boss’s boss at WNYC said to me, if you stay in New York, you’re going to end up fetching coffee and being frustrated with your lack of upward mobility for a long time. You should leave New York and try to work at an NPR affiliate elsewhere. So I started applying to different public radio gigs all over the country, and I ended up moving to Wisconsin, where I had been hired to create a statewide news magazine program. I was 22, and I was excited to have a job but hesitant about moving to a place where I knew no one. It worked out. I spent two and a half years there, and I learned a lot. Honestly, spending a lot of time on the East Coast, it's good to get away and experience the politics of other states, particularly a swing state whose state-level political conflicts have, in many ways, become national conflicts. There’s a lot to Wisconsin, it's a beautiful place with friendly people and good food, but after two and a half years, I decided that I wanted something different, and so, again, I took a risk, quit my job, and moved back to New York without a job.

And then what happened?

While I was in Wisconsin, This American Life had published Serial, making the whole podcasting and audio industry explode. There were suddenly more people making audio than just the public radio stations, and there were many more opportunities. I also had a lot more experience because I had spent two and a half years making audio in Wisconsin, so I had a lot more success freelancing when I moved back to New York after being in Wisconsin than before I had left. My boss’s boss was right. I reported on all kinds of things, I even did a series on artists trying to make it in New York City, I did some campaign reporting, and ultimately started freelancing at FiveThirtyEight, which was launching a politics podcast. That is what got me on the path to what is now my job, hosting [and producing] the FiveThirtyEight politics podcast and covering national elections.

So, I listen to a lot of podcasts, including FiveThirtyEight. You interview a lot of politicians for your show, and you’re quite a direct interviewer. I wonder, are there any questions you find hard to ask?

By nature, I am a peacemaker. I am a middle child, and, in many ways, when I was younger, before I went to St. Stephen’s, I was a naturally shy person. If you want anyone to bring you out of your shell, ask Italians. My time at St. Stephen’s went a long way in teaching me how to be more confrontational.

It can feel awkward, but it's our job in journalism to be confrontational and hold people accountable and ask difficult questions.

Politicians are usually bad interviews; they stick to talking points that are well-rehearsed and somewhat empty; if you want to have a meaningful conversation with a politician, you have to get them off their talking points and, often, the only way you can do that is by asking questions they’re not expecting: blunt questions, diving straight into the conflict of the day even if it can sometimes be uncomfortable, you have to embrace that as a journalist because that’s your job. And, eventually, you get used to the adrenaline, and it can be fun. As journalists, we work for the companies we work for, but we also play a broader role in society. There’s a reason we’re protected under the First Amendment; we have a duty to our fellow citizens to get answers for them and hold public officials accountable. If it weren’t uncomfortable, I wouldn’t be doing my job.

You’ve talked on the podcast recently about the danger of polarization in the U.S. Congress and the problem of “cult of personality politics;” in your opinion, are these two phenomena linked?

I think they can be, but a cult of personality can exist without severe partisanship: think of Reagan and JFK; they relied on a politics that was very much built on their personalities, during a less polarized period in the U.S. If you form a cult of personality around a deeply polarizing person, the result can be increased polarization, and that’s what we’ve seen in America, and that’s what we saw with Trump. I think that, in many ways, symbols and personalities have become important determinations of voting behavior. [However], you can’t solve political issues through force of personality alone. Our American system--both our presidential system and our media ecosystem-- is set up in such a way that it creates an environment where the way you win elections is, in many ways, by creating a cult of personality. This happened with Obama. Biden is an exception, but there was so much antipathy for Trump that Biden didn’t need the cult of personality. In a parliamentary system, the leader of a party within a parliament is the person who becomes the Prime Minister. The entire country does not vote for one person who becomes a vessel for everyone’s hopes and dreams. We are uniquely set up to create a politics that is based on personality cults. That can be dangerous. At the same time, we have lots of examples throughout history of people being able to do good through the force of their personality, think of people like Nelson Mandela or Gandhi, a lot of our heroes. If people believe in you because of your charisma and how you’re able to inspire them, you can do good things (and can also do terrible things, of course).

What do you consider your greatest achievement or one of your most significant accomplishments?

First and foremost, the relationships that I have in my life. I’ve worked hard, I’m an ambitious person, and throughout my 20s, I worked to get a foothold in a career that I found exciting and challenging. I’ve found it rewarding to make a place for myself in this industry, but, at the same time, no job is ever going to console you when you're down; your job’s not going to go out to dinner with you or go to your birthday party or give you the feeling of belonging and community that you get from the relationships that you build along the way. So, first and foremost, having a lot of close friendships, many from my time at St. Stephen’s, from college, and from the journalism industry itself, is the most fulfilling part of my life and maybe even my most significant achievement.

When it comes to my work in journalism, hosting the FiveThirtyEight politics podcast during a tough 2020 election and being honest and clear-eyed about the challenges we were facing as a nation and the uncertainties of the election was an achievement. During election week, I slept maybe 15 hours over five days. I was delirious by the end, but getting through the 2020 election feels like an achievement.

I am also proud of the long-form work I have done and my work in narrative journalism, and the series I have worked on. One of my focuses has been democratic structures and how systems shape outcomes in American politics. Two series in particular that I worked on were one on gerrymandering and another on how we set up our primary system in America; both of those can lead to undemocratic and dissatisfying outcomes. Understanding how our systems shape our politics is important to me.

What do you enjoy most about what you do?

I like learning new things and going out into the world and talking to all kinds of people and getting all different perspectives, especially from regular people, not just politicians. I enjoy meeting people where they are and understanding their experiences, their understanding of American politics, their wishes, their fears, and their thoughts. As a journalist, you get to meet and interact with people that you might not ever meet in the normal course of your life, and that’s a privilege.

Also, [I love] learning new things. I loved school. Journalism as a career is, in some ways, the closest you can get to the work that you do in college other than being an academic. [In journalism], you are faced with a set of questions, uncertainties, or challenges. You get to go out into the world and find answers, talk to people and read everything from academic journals to chatrooms to understand the world and then synthesize that information so that your audience can have a better understanding of the world.

What are some of the most important lessons from your professional experience that you would like to share with the next generation of St. Stephen’s graduates?

When you go to school in Rome, you can feel like you’re already an adult; you have so many experiences that kids your age don’t have, and you get to meet different kinds of people from all over the world, but it’s essential to keep in mind that this is still only one perspective. There are a lot of other perspectives and experiences out there waiting for you to interact with them.

The time that I spent in Wisconsin, a very different place from Rome, was just as eye-opening as the time I spent in the center of Rome. Embrace uncomfortable situations that make you question your assumptions and your experiences.

Also, I can’t speak so much to Italy, but at least in America, many of the hierarchies that have shaped who has power and who has opportunities are being questioned and are starting to break down. In that environment, people with power can feel threatened and awkward, but it's an important thing to embrace and appreciate as it creates opportunities for all kinds of people. Frankly, even as someone who got to go to St. Stephen’s--which is a privilege in its own right-- I have had opportunities because of the way the hierarchy has broken down and the way that the internet, social media, and all these new forms of media have created openings for new voices. When I couldn’t find a job for a year after college, I started my own podcast, and that sounds like a trope now because everyone has their podcast. Still, back then, it was a little rarer, and that’s a large part of the reason Wisconsin Public Radio hired me as a producer to start creating a brand new show even though I had never had a full-time job in journalism before. The way the world is changing can be scary for some people, but it can also be exciting.

You can listen to the FiveThirtyEight podcast on your favorite podcast streaming platform or directly on their website