Cheers to Ten Years: An Exclusive Interview with Co-Founders, Trena White & Jesse Finkelstein

Oct 11, 2023

Pictured above: Jesse Finkelstein (left), Trena White (right)

On a Tuesday afternoon in September, our Director of Sales & Distribution asked a question on our Page Two Community Slack channel: “What event in your life do you feel has shaped you the most significantly?” 

Trena White said the following: “The day Jesse Finkelstein came back from a family trip ten years ago and told me that she and her husband, Yaseen, had talked it over, and they were all in. Jesse was ready to build a company with me. So we did!”

October 3, 2023 marks the ten-year anniversary of this birth child called Page Two. Ten years of asking thoughtful questions, making meaningful connections, launching new and exciting career paths, and shepherding big, bold, game-changing ideas into the world. To celebrate the accomplishments of our co-founders, Trena White and Jesse Finkelstein, we’ve decided to dig deeper into the business partnership that has made Page Two the incredible company that it is today. 

How did you arrive at the name Page Two? What do these words represent for you?

JF & TW: Page Two has several different meanings. We believe in the power of partnership, with two (or more) heads being greater than one. That’s at the heart of everything we do. Further to that, we launched the company at a time when people were talking about Publishing 2.0—the next phase of publishing. Whether you’re thinking of the digital shift that enables so many new book formats or a new generation of publishers like us, the concept of a second phase is compelling. And finally, if a book is really good, you never stop reading at page one; you always flip to page two!

What have you learned from your co-founder over these past ten years?

TW: I’ve learned the importance of slowing down and considering every angle before making important decisions that could have long-term implications. That’s not my nature, and I’m grateful Jesse has that ability, while being a visionary at the same time. The incredible empathy and kindness she brings to every single conversation has also made me a more thoughtful person.

JF: I’ve learned that the best entrepreneurs are visionary and ambitious while also staying laser-focused on the execution plan. You can’t have one without the other. I aspire to that and work at it, but Trena has been that way since day one, and it’s been a gift to me and to Page Two. 

How do you feel you complement one another?

JF: We’re similar in all the important ways, which makes it easy to develop shared core values, priorities, and goals. And we’re different in ways that support the company’s leadership and growth. Our distinct publishing backgrounds allowed us to launch a holistic offering with deep expertise in every part of the process. And our distinct approaches to entrepreneurialism help as well: Trena’s always had a vision to build her own company, whereas I always had leadership aspirations that drove my career goals but didn’t envision myself to be an entrepreneur. Good thing I met her, otherwise I’d be working for someone else and wouldn’t know what I was missing!

Where does your bravery come from? Were you a leader in school? As a child?

JF: I don’t think I’m especially brave but I had some trailblazing role models in my family, including pioneering immigrants and Holocaust survivors who represent true bravery to me. In terms of leadership, I made a deliberate effort to develop those skills. I remember being pigeonholed as a shy kid because I was relatively quiet. But I didn’t actually feel shy. When I entered high school, I joined the student council so I could meet new people, and that confirmed my love of building relationships with many people, at different levels. I’ve stepped out of my comfort zone many times since then, and each time I’ve learned that it’s totally worth it. 

TW: I don’t think of myself as brave. Determined maybe. And I like to try new things and am not easily daunted by change. I think those are the traits that led me to launch a company with Jesse more than bravery. Probably a healthy dose of naivete, too, since I didn’t know a lot of entrepreneurs at the time and didn’t realize what a massive undertaking building a business would be. As a kid, I always worked hard on my own projects, like I had something to prove to myself. My dad has similar characteristics, and I believe I inherited many of these qualities from him.

What is one book that has changed your perspective about life? That has moved you to take action?

TW: Editor to Author: The Letters of Maxwell E. Perkins. Perkins was a famous book editor who worked with F. Scott Fitzgerald, Thomas Wolfe, and Ernest Hemingway, among many others. That is the book that made me want to become an editor, the role I started with in book publishing before becoming a publisher and entrepreneur. Perkins’s letters to his authors were magnificent: direct, careful, thoughtful, and full of warmth. He would deliver insights about what wasn’t working in a manuscript, while trusting in the authors’ brilliance and that they would have the solutions. To me this old-world correspondence built on a deep foundation of trust and respect between two bright minds is still a perfect model for the kind of relationship an editor or publisher should develop with their writers. 

JF: I loved Zora Neale Hurston’s fiction, and in university I wrote my honors thesis on her autobiography, Dust Tracks on a Road. Hurston was a Black American writer who was well known in her time, but she died in obscurity, partly because the way her political views were expressed in her autobiography made her unpopular among many of her Harlem Renaissance peers. When I researched the publishing history of Dust Tracks, I learned that Hurston’s editors changed much of her original text to create a book that they felt would be more palatable to a white audience, and the devastating result was a book that didn’t represent Hurston’s voice and story accurately. That opened my eyes to the power dynamics involved in the publishing process and motivated me to seek out employers and colleagues who were creating positive change in the book industry. 

What has been your proudest moment or achievement since launching Page Two?

JF: I feel pride and joy in this company all the time! But three great moments stand out: when we were nominated for a major entrepreneurship award, when we made it through COVID with a full team and author roster, and when my kids did “take your child to work day” and confessed that they thought my job was way cooler than the other parents’!

TW: There are so many! The two times our books have won booksellers’ choice awards, the time Jesse and I were nominated for a women’s entrepreneur award, the way our team rallied during the earliest months of the pandemic—those are just a few that come to mind.

What has surprised you about your experience running your own publishing company over the past ten years? Did you imagine this life for yourself?

TW: In some ways, I did imagine this life for myself. I was the kid who created newspapers about our neighborhood and sold them door to door. I was always thinking about business ideas and I always loved books, so it makes sense that eventually they came together. But I never could have launched Page Two without Jesse. I never could have imagined having such a dream business partner and a dream team, and working with the stellar authors that we do. Ten years in, I’ve learned so much about what goes into building a great business, and I’m grateful for all of the people who’ve helped us along the way.

JF: I imagined working in book publishing. It’s all I ever wanted to do. But I never envisioned running my own business. In the end, my job is more rewarding than anything I’d ever imagined. I work with people I respect and admire; I get to do so many things I enjoy; and I have freedom, autonomy, and prosperity. I’ve worked hard and I’ve had so much good fortune.

What would you like to see change about the publishing industry in the next ten years?

JF: Increased visibility of underrepresented authors and a diversification of book publishers and sales venues. Also, increased leadership roles assumed by women and people of all other backgrounds who have traditionally been shut out of leadership positions in the book industry. 

TW: The continued health of independent book publishing and sales channels. More books published by underrepresented authors.  

Do you have a dream project that you would love to work on? Or a certain topic that you would love to see expanded on in a future Page Two book?

JF: We are perpetually interested in books that take a topic of interest and turn it on its head. Like our author Liane Davey, whose book—The Good Fight—takes the surprising position that we need more conflict, not less (we just need to do it better). The more books that challenge our assumptions, the better! 

TW: We’ve been doing some important publishing of Indigenous authors and recently partnered with a First Nation to tell their story in book form for the first time. We would like to do more of this, supporting Indigenous people with telling their stories in ways that respect their ownership of their ideas and their work.

At Page Two, we focus on helping authors to achieve their own personal goals above all else. What are your own goals that you are working on this year, both at Page Two, and in your personal lives?

TW: My two little boys grew up alongside the company; my eldest was just three months old when Jesse and I began building Page Two. Recently, we’ve been focused on building our leadership team at Page Two, and for me part of the joy of doing that is that it means ten years in, I’m finding more equilibrium between my work life and family life than I’ve had before. 

JF: I attended a mentor’s retirement party shortly after launching Page Two. At the time, I felt terrified about my new self-employed status, and anxious about whether we could realize our vision for the company. I chatted with my mentor, who’d had an illustrious career, and thought to myself, He’s really made it. He must feel great. But after sharing some pleasantries about his newfound freedom and travel opportunities, he leaned in close and whispered, “You know, Jesse, it’s all good, but nothing is as exciting as building something.” I’ve kept that in mind over the past decade when I’ve felt worried. I’ve tried to remind myself that I’m privileged to do what I do, and even the stressful moments have valuable lessons in them. It’s a great adventure, and I aim to savor it.