CEO Jean Smart on Being the First and Only
May 30, 2023
Jean Smart is the Founder and CEO of Penelope, a fintech company disrupting retirement solutions for small and micro businesses. Prior to her startup career, Jean was Managing Director and Head of Business Strategy at UBS. Jean has extensive experience as an accomplished global executive, and successfully develops and manages thriving marketing teams and business organizations.

Jean has also held senior roles as the Global Head of Marketing for Private Client Solutions with Citigroup’s Markets and Securities Services division. Jean has served as a board member for a number of different organizations where she provides financial and digital insights including the Cancer Support Community’s Global Digital Advisory Council. Jean obtained a BA from University of California, Berkeley and lives in New York City with her husband Nick, daughter Penelope and poodle Zoom.

Since I was a little kid, I’ve frequently been the first and only—whether that’s in the classroom or the office. And while I’ve gotten used to it (for the most part), there’s still a part of me that is always a little shocked to be the one Asian in the room. But it’s also a defining part of my story, and why I am where I am today.

I’m the oldest of three kids. When my parents immigrated to the U.S. in the mid 1970s, they left me and my brother and sister in Korea with my grandparents because they thought it would be too hard to make the move with three small children. We were apart for a year. I wasn’t much more than 4 years old, yet I became something of a surrogate mom to my brother and sister. When we were finally reunited with my parents, my little sister, who was about 3, asked my mom if she was her mommy. My mom burst into tears.

We lived in a little apartment in Montclair, Calif., and the first month all five of us slept in the same bed. We later moved to Claremont because it was a proper middle class neighborhood, and my parents heard the schools were good. We spent all our time with family—I had 11 cousins. My parents opened a small grocery called Andy’s Fine Food Market, and then later on a dry cleaners and eventually they owned a couple of Japanese restaurants (Korean food wasn’t as popular at the time).

It wasn’t until I went to kindergarten that I first met any non-Koreans. At 5 years old, I was so shocked by the kids, who seemed in my eyes to have “yellow” hair, and everyone speaking English. I was the only Asian kid in my class. It was the first time since coming to the U.S. that I felt different.

And there were so many things I didn’t understand. Benign things like sports, and then more complicated and uncomfortable things like why the kids called me “banana” or “Twinkie.” As the only Asian in my classroom, I didn’t have an obvious ally who could help me navigate this new, sometimes unwelcoming, world.

In the intervening years, I’ve been the first and the only more times than I can count. And I’ve gotten used to it. I learned to code switch—during the school week I had my American friends and on the weekends I spent time with my Korean family. Of course, I didn’t understand that what I was doing was code switching—I didn’t learn that phrase until years later. But I was definitely one type of Jean at school (a quiet, hard-working, rule follower) and another Jean at home (way more fun and goofy).

It wasn’t until I went college at UC Berkeley and found myself surrounded by so many fellow Asian students that I wasn’t an only for a little while. It was almost a reverse shock there. But also a luxury, and I loved building a community of Asian friends who really understood my experiences.

After graduation, I went into financial services, where for the first time I felt some anxiety about my abilities. I thought you had to be so smart—amazing at math and a good communicator to boot—to have a white collar job at a big bank. But my code-switching skills continued to help me succeed. Sure, it helped that I was smart, but I also was good at playing the game even with the deck stacked against me.

Asian women face an uphill battle in their quest to land executive roles because people don’t see them as leaders. There’s a perception that we’re quiet, reserved, and thoughtful, and unfortunately, those characteristics aren’t typically associated with leaders. For what it’s worth, I’m none of those things. I’m pretty loud and talkative and effusive. But I also think there’s a lot of power in being quiet and thoughtful.

While I was used to being the first and the only, by the time I reached my early 40s, I knew it didn’t feel right. I wanted something more. I liked that my work in financial services had provided a steady career and good pay check that allowed me to support my parents and have my own family. But I also felt restless and wanted to feel good about the work I was doing. And honestly, I wasn’t getting any younger. Maybe it was mid-life anxiety, but I spent a lot of time wondering what I was going to do with the rest of my career.

And then COVID happened. And George Floyd. And the increased violence against Asian Americans. After I learned about the murders in Atlanta, I immediately called my mom and told her not to leave her house in California. And then I called my babysitter to make sure my daughter was OK.

I was scared and angry and tired of being beholden to others. I wanted to make a change, and I wanted to have a direct hand in making life better for average Americans. I saw there was an opportunity to stop code-switching and marry the two sides of my personality—brave, outspoken Jean, daughter of immigrant small business owners and hard-working, thoughtful Jean who rose through the ranks of the biggest financial institutions. And as an Asian woman who’s spent her whole life navigating rooms where I’m the first and only, I had a clear vision of the kind of company I wanted to build.

I started Penelope because my parents were small business owners with no retirement savings. And I named it after my daughter because I want her to be able to build on the generational wealth I’m handing down to her. I don’t want her to be my retirement plan.

I’m proud of the company we’re building. It isn’t easy, especially as an Asian female founder trying to raise venture capital. And it’s also a little bit scary. But I don’t question why I'm doing it. I deeply believe in our mission to help small business owners provide their employees with a 401(k) that can help them build their own generational wealth.

I might still frequently be the first and the only—but I know I wouldn’t be who I am today without that experience.



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