“It took me many years to build the confidence to fight for my ideas” : A Conversation with Leslie Shipman

Amy Gall chats with Leslie Shipman of the Shipman Agency about how the most important ingredient to building a successful small business is love.

After spending twenty-five years in the literary nonprofit world, building nationwide reading programs, hosting events with hundreds of attendees, and eventually becoming the assistant director of the National Book Foundation, you might think the last thing Leslie Shipman would have wanted was to leave it all behind to start her own business. But sometimes, the bigger the risk, the greater the reward. “Being my own boss is literally one of the greatest things that’s ever happened to me! If I have an idea that I think will work, I act on it . . . and the freedom to say yes rather than battle a zillion noes is exhilarating.”

It’s not only exhilarating; it’s a model that’s proved to be very successful. When Shipman launched the Shipman Agency in 2017, its sole focus was booking authors for speaking engagements. But in four short years, she has built the agency into a one-stop shop for over one hundred clients to include a literary agent, a book publicist, and The Work Room, which gives her authors the opportunity to teach online classes and seminars to the public.

Before becoming the founder and president of the Shipman Agency and her work at the National Book Foundation, Shipman was the director of the Bronx Writers Center. She is also a poet with an MFA from the Program for Writers at Warren Wilson College, and her work has appeared in the Kenyon Review, BOMB, and elsewhere. I spoke with Leslie via email about staying profitable during the pandemic, how being a writer influences her approach to representing authors, and how the most important ingredient to building a successful business is love.

Amy Gall: How did you start the Shipman Agency?

Leslie Shipman: The last thing I ever expected to do was start a business. I had been in and around literary nonprofits my entire career and I thought that’s where I would stay. But life intervenes and inevitably throws some challenges in your path when you least expect it, so after eleven years at the National Book Foundation, I decided I needed a change. Having no idea yet about the business, I did some consulting work with PEN for a while and then was approached by a speaker’s agency to work with them. I had a dear friend who had said I’d make a great speaker’s agent because I had done so much event work over the years and knew so many writers. I decided to give it a try. In the end, that agency was not a great fit for me, but while there I signed a bunch of clients who became the first clients of the Shipman Agency when I decided to go off on my own.

AG: How do you think being a poet has given you particular insight into what writers are looking for in a speaking agent?

LS: I gave a talk to some MFA students not too long ago, and one of the things I wanted to impress upon them is that the vast majority of people in publishing and publishing-adjacent businesses do this work because they love books, they love reading and writing, and because so many of them are writers themselves. If you enter this business to get rich, you’d be better off somewhere else, because we know salaries are notoriously low (and unfairly low, but that’s another conversation).

If you don’t love books and everything that comes with loving books, how can you bring any passion to what you do? So being a poet is 100 percent linked to understanding what’s at stake for folks as they think about a career as a writer. Part of what’s at stake is love​​—writing is difficult and lonely, writing is joyous and liberating; these truths exist simultaneously. If my approach to this business isn’t grounded in that love of both the difficult and the joyous, then I’m just like any other cookie-cutter corporate agency.

AG: You mentioned working for many years in literary nonprofits. What lessons did you take with you for how you approach running your business?

LS: I love this question! I came up in the business in an era when businesses weren’t supposed to be “political,” an idea I really hated. Why should a business not take a stand? You’ll alienate customers? Well, if those customers are white nationalists, no thanks, don’t really need your business! What has been true since I started this business is that I haven’t changed and the things I care passionately about haven’t changed, so when you look at my roster of clients, you are seeing an expression of those voices and ideas I believe we need more of. In a sense, I have even more freedom to be “political” now than when I worked in nonprofits because of the fear of alienating donors.

Why should a business not take a stand?

AG: What are some of the most gratifying moments of doing this work? What are some of the most challenging? And how have you met those challenges?

LS: The most gratifying is asking for a large fee for a writer for the first time and getting it! Regardless of where they are in their careers, so many writers underestimate the value of their labor—going to colleges and universities, giving readings, doing class visits, craft lectures, faculty dinners. All of those things involve labor, and writers deserve to be appropriately compensated. But artists in this country have been taught to believe that attention is enough, that an artist’s labor isn’t real labor—an idea I will spend the rest of my days fighting. So it feels like an immense victory when we can pull those big fees.

My biggest challenge is saying no to folks. In a perfect world, I’d love to say yes to every writer who has looked at what we’re doing here and wants to join us, but I have to be very careful about taking on too much work. I pride myself on the accuracy of the work we produce; when we send an itinerary to a client, it’s important that the client trust the accuracy of that information; otherwise, what good are we? And all of this work is extremely detail oriented and labor intensive. I am beyond lucky to have two amazing women working with me—Cassie Archdeacon and Katie McDonough. I’d be lost without them.

AG: During the pandemic, when no one was giving in-person readings, you smartly pivoted toward the online-classroom model, where authors could run workshops on craft, novels, short stories, and essay writing. Can you tell me more about how that came about and what the response to it has been?

LS: Of all the things I worried might bring down my business, a pandemic was not on my bingo card! So when I absorbed the reality of what was happening—the cascade of events being canceled, the thousands of dollars being lost, yes, by the business, but even more so for my clients—I had to do something and do it quickly. And as a lifelong student of the craft of writing myself, why not start offering classes? And this goes back to your question about being my own boss. The only people I had to convince that this was an idea worth trying were my clients, and they were totally game. And it was exciting, in a time of great fear and confusion, to offer something like The Work Room to not only my clients, but to the community at large.

The first lockdown happened in March 2020, and our classes were up and running in June, with faculty like Garth Greenwell, Carl Phillips, Sheila Heti, Jordy Rosenberg, Alexander Chee, Patricia Smith, Kaveh Akbar, Maria Dahvana Headley, Andrea Lawlor . . . how could we go wrong? The response has been amazing, and something that started as a temporary response to the pandemic is now a permanent feature of the agency. And the way I think about how this dovetails with my role as a speaker’s agent is this: My number one job is to put as much money as possible in my client’s pockets, so why not offer them an additional revenue stream? So now, when a writer comes here, they have more than one way to produce income for themselves, and I love that.

AG: What advice would you give to younger folks—particularly young women—who are thinking of starting their own literary businesses?

LS: First, stay close to what you love. That really is number one in any career. But second, and specifically for women: Trust yourself, trust your instincts. The patriarchy has done an excellent job of sowing doubt in women, this constant question of “are we enough”—smart enough, competitive enough, confident enough, et cetera. I can’t help but recall all of the men I have fought with in my thirty-year career and how many times I turned out to be right in the end! It took me many years to build the confidence to fight for my ideas, but every single one of those fights, even the ones I lost (and there were many), advanced my faith in my own abilities. I’ve lost many battles over the years, but when I look back at my life and career now, I realize that I won the war.

AG: Is there anything you’re particularly excited about for the future of the Shipman Agency?

LS: I’ve got a million ideas swirling around, but none of them are far along enough to discuss yet. But just expect us to continue to break the mold and redefine what an agency can be. Stay tuned!

AG: Finally, and this is a question I love asking poets: What is your favorite thing about language?

LS: Sound! Words are ultimately units of sound first. Meaning is secondary. (You can tell I’m a poet!) I love the sounds of a poem washing over me, the rhythms, the beauty of syntax. I could go on! My first love was music—I’m a proud failed musician—but poetry is music—it’s origins are in song—so I have the best of both worlds.