Interview #11: Turning Survival Skills Into a Media Empire, With Polina Pompliano

It’s not every day that you get to interview one of your role models — and today I am deeply grateful, honored, and excited to be interviewing someone who has been an inspiration to me for years: Polina Pompliano. She is the founder of The Profile, one of the most prominent newsletters on Substack, which profiles the most successful and fascinating people in the world.

Though it seems common today for journalists to leave traditional media outlets to start their own publications, Polina was one of the first, if not the first, to do so back in 2020. She has interviewed personalities such as White House Communications Director Anthony Scaramucci, real estate legend Ryan Serhant, and New Balance CEO Joe Preston. She has also done in depth-studies of celebrities like Dwayne “The Rock” Johnson (who also loves Polina’s work, too!). In 2023, she published her debut book Hidden Genius, about the mindsets of the world’s most exceptional people.

Previously, Polina was a reporter at Fortune, writing their famous newsletter Term Sheet, which covers the latest news on tech, venture capital, and M&A. In today’s chat, we cover her early childhood immigrating from Bulgaria to the U.S., how she gathered the courage to leave her dream journalism job, and her tips for reconceiving the shame and struggle of our “failures” in a way that will both excite you and make you feel calmer and wiser at the same time.

I hope you take away as much from the conversation as much as I did.

You've talked a lot about your interest in human behavior — coming to the US when you were young and learning to read people's body language since you couldn't understand what they were saying. Did you ever think about any other jobs besides being a journalist that would involve that skill set?

I never saw that as a skill set. I saw it as survival, to be honest. This week actually marks 25 years since we moved to the US from Bulgaria. It was so much about human behavior, observing people, not being able to communicate. Communication is such a big part of my life today that I cannot imagine having to start over again in the same way. But it did teach me a lot — you see how people are sitting, the way they're talking, what they do with their hands, whether somebody's introverted or extroverted.

But actually, when I was a kid, I thought I would be a chemical engineer because both of my parents were chemical engineers. Once I realized that journalism could pair research, writing, and social skills, and you could observe humans and behavior and note the way they move through the world — that was the perfect pairing for a career for me. And once I discovered that, I never looked back.

When you think back on your life, what would you call some of the main challenges you've been through?

The biggest challenge was probably learning the societal norms and cultural norms of moving to this country. But the other thing, for me, if I had to think about my life's theme in terms of challenge, it's not necessarily that I tried and it didn't work out. It's more that I didn't try, and I don't know if it would have worked out.

The reason leaving Fortune and doing this on my own was such a big thing for me is because it was a big risk. And as someone who is an immigrant, I wanted to mitigate risk. So my whole life became about mitigating risk.

Very rarely do we talk about challenges being the path not taken, the risk not taken, the venture not taken. So I would say it's a mix of having enough confidence in myself to know that I have the skills to have it work out, and being able to take the leap to something that has potential upside. Versus only seeing the downside.

Are there any specific things you wished you tried earlier?

When I was in college and I graduated, in my head I always wanted something bigger. Success meant living an extraordinary, full life. But I didn't quite have the mindset to get there because I hadn't known people who thought that big. My family raised me well, but it was always with "you better bite off as much as you can chew and not more."

So I wish that I had, while still in college, started something on my own — whether it was a company or a newsletter or just anything, a hobby that I did only for myself — because I had dreams of something bigger instead of only following somebody else's checklist.

I went to the University of Georgia, and a lot of my friends there — their biggest dream was to live in Atlanta. To me, that wasn't big enough, and I knew that. But instead of acting on what I wanted, for a few years I actually did the safe thing and worked in Atlanta. I was constantly lying to myself, trying to talk myself into being satisfied with less than what I really wanted.

I think it's a mindset difference. I was not playing to win. I was playing not to lose.

I think that's very common for anyone from an immigrant family.

My parents were 28 and 34, and I was 8 when we came here. I noticed that for them to accept this new mindset was way different and way harder than it was for me. I specifically remember them saying, "Can you believe Bill Gates and Warren Buffett are billionaires, yet they dress so horrible? They don't wear suits and ties." That was a very American thing — to dress however you like, even though you have all the money in the world.

For my family in Bulgaria to move to the US — that was the biggest risk you could think of. Leave your country, leave your family, your friends. Go build something where you don't know a single soul in America. So that was huge for me. I was like, "What else? What's next? How can I build on top of this?"

As a kid, I remember trying a lot of things — acting, singing, soccer — all these things that I wasn't necessarily great at. But my parents still let me try. So in that way, it let me try a lot of things and take small risks so that I would eventually hit on something I was good at. And that's exactly what happened in high school, when I signed up for an elective newspaper class. That hit — I was good at it and I liked it.

If you take the small, very tiny risks, eventually you are able to quit your job and do something without necessarily the fear of crushing failure.

You started The Profile while working at Fortune. Were there any other concrete gradual steps like that you took?

Working on The Profile was a risk, but it was a calculated risk. And the beauty of that is I never started it thinking it would be a business or that I would quit my job. So everything was very gradual. I started it because I wanted a conversation starter with family and friends. I was constantly talking to them about stuff I was reading. So I was like, let me just formalize this and put it in an email, send it to family and friends. For a long time I only had like 20 subscribers, all of whom I knew.

But as life would have it, six months after I started The Profile, I started writing Term Sheet at Fortune, which is another newsletter. And those people also liked interesting things and reading about people and business. So some of them went to my Twitter, they saw that I had a link to my personal newsletter, they signed up and it just slowly snowballed until you reach a point where you're like, "Could this be a thing that I do on my own?"

When I decided to leave in March of 2020, at the time, I was the first legacy media reporter to leave their job to do this full-time. I didn't know any newsletter writers. The only person I knew was Robert Cottrell who wrote "The Browser.” There was nobody else who had left their job at a media company to do this. And then of course during the pandemic there was like an avalanche of people. But doing it without knowing "Could this work? Do people make money like this?" It was all very new.

It's one thing to do it when you have a safety net of "Oh, I'm doing The Profile on the side, but I have my job at Fortune." It's another thing to be like, "I'm jumping with no parachute. I have no idea what's going to happen." But when you go all in and you burn the boats, there's this fire under you that helps propel you, and you actually end up overcompensating and succeeding just by nature of "I don't want to fail."

What are the most unexpected things that you've learned from going off on your own?

One of the more unexpected things is how much I love setting my own schedule, deciding what I do, who I meet with, where I spend my time, versus being on somebody else's time. I always thought that I thrived in a structured environment with a boss guiding me on what to do. But there's a level of freedom, and if you're a person that is intrinsically motivated, then entrepreneurship is actually a great avenue.

Here's actually a good example to circle back to what we were talking about — challenges that I wish I had taken sooner. One time recently, in December, I was at dinner with my husband, and I was like, "I don't know, what's next for The Profile? What should I do?" I felt kind of stuck. And he was like, "Well, it's called The Profile. Why don't you write profiles?" And I was like, "What?"

I never thought of — like, yes, I should write original profiles. In the eight years that I've done it, I have not written a single profile. Like, what? That's why people come here. So now, starting in January, I published my first on Anthony Scaramucci. Right now I'm working on one on Ryan Serhant (side note: this profile is absolutely incredible).

But the point of that being — I think if I'm honest with myself, the reason I never wrote profiles, which is what I love doing and why I started this in the first place, is because I was afraid: "Nobody will answer my calls or emails or take me seriously because I'm not in a big media organization." So I kind of held myself back from what I actually wanted to do in order to not fail, you know?

You have what many people would consider a dream job, you’re part of a power couple, and you’ve built your own family. I'm sure a lot of people think, "This sounds like a dream life." What do people not realize if they're on the outside?

That there's a lot of chaos. I'm constantly trying to make order of the chaos. I think when you have a job, you're doing all this stuff, you have a partner, you have kids, you're just trying to keep your head above water. But I was talking to one of my friends recently, and I was like, "Dude, it feels like it's just constant chaos." And she was like, "Yeah, but one thing about you is I actually think you secretly like the chaos." And I thought about that, and I was like, I kind of do.

Something that my husband and I always ask each other before we make a big decision that could lead to potentially more chaos is: "Will this help us lead an extraordinary life?" The whole idea is, I don't want to live an ordinary life. Like, I didn't move to New York for that. I like everything that I do. I just want to strive for the best. So will this choice get us closer to getting there?

I feel cheesy asking this because this is your question at the end of interviews, but it’s a great one. What does success mean to you, Polina?

Success to me is living an extraordinary life. And I think what that means is not a linear path. It’s a life where you succeed at something you set out to achieve — then you fail miserably. You're hit with something unexpected. You think you can never get up again. Then you take the lessons you learn from that and you're like, "I'm not gonna stay here, I'm gonna try this again." You get up, take the lessons, build something else. Whether it's a life, a family, a career, a startup, you build something else in whatever direction you decide to go. And then you come out on the other end with those lessons.

Hopefully you're able to share those lessons either with the world or other people behind you, or help lift somebody up when they are in that spot. A lot of people call it "before the fall” and “after the fall." Before the fall, you're just kind of like, "I can do anything." And your ego is quite big. And then once you fall, you're like, "Oh my God, everything can change in an instant." After that, you have more humility and more texture to the way you see the world. Instead of "I'm the greatest" you learn: "Hey, how can I take the lessons that I've learned and build something sustainable instead of something just very short-term for the glory of it?"

For someone who is going through a hard time —or let's say is in the process of falling, as you put it —what would be your advice to them?

The thing that I've always kept in mind, even though it's hard to see it in the process, is that this is very, very temporary in the grand scheme of things. When you’re falling, it's horrible. You can barely get out of bed. You think it'll last forever. But again, no great feeling and no horrible feeling lasts forever. It's all just very temporary. You see it a lot when you have kids. Every stage is hard in different ways. And the thing is that now in hindsight, I'm like, "Oh my God, that was like a blip in time." But at the time I was like, "We're gonna be in tantrums forever. This is horrible." And you start spiraling out of control when it's just like, this is a temporary phase.

And I think the word "phase" is very important because people see their lives as this continuous thing. But I don’t think so. This is just a phase in your life that you will get out of and maybe even miss the hunger of it, the grind, the struggle when you've made it to the other side. So it's like seeing it as a temporary thing that you will eventually get out of. But while you're in it, honestly, just take all of those feelings in. Because you'll never feel as bad again, probably.

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Thank you so much for reading!

You can subscribe to The Profile here and check out her book Hidden Genius here.

I’d love to hear your comments below — and stay tuned in the next post for my reflections from my conversation with Polina!