Jeanne Darst on Landing Every Author's Dream Deal (and What Happened Next)

Jeanne Darst's story is what happens when everything goes right—and then you realize "right" is more complicated than you thought. After years of doing plays for 200 people in Vermont, she hit the publishing lottery: a bidding war sparked by a “This American Life” appearance that had publishers hunting her down by the next morning. Riverhead Books won with serious money, the New York Times loved it, Vogue excerpted it, HBO optioned it and she wrote the pilot. It was the full fantasy—except the show didn't get picked up (Girls was coming out), and she spent the next decade in the Hollywood machine. Her TV writing career was a success—she got a series of TV staff writing jobs—but her second book, Dad's Trying to Kill Me, couldn't find a publisher (despite glowing rejections). Now she's back to putting on shows while continuing to write, because sometimes the dream coming true teaches you what you actually want.Episode Highlights:How Jeanne's This American Life story triggered a massive publishing bidding war overnightThe strategic decision to write a proposal instead of submitting a completed manuscriptWhy Jeanne chose Riverhead and editor Sarah McGrath over the highest bidderThe simultaneous media blitz: book launch, Vogue excerpt, and This American Life featureHow HBO optioned the book before publication, leading to pilot writing opportunitiesThe reality of post-success hustle: why the dream is "just the beginning of heartbreak"Jeanne's second book rejection and the lesson about going to small pressesWhy she's returning to grassroots theater after a decade in HollywoodThe father-daughter dynamic when children outachieve their parents professionallyKey Takeaways:Two years of persistence can lead to overnight success Agents and gatekeepers are "smart secretaries" - you must drive your own careerWomen wait 8 months to resubmit after rejection; men wait 3 daysBig advances don't guarantee book tours or sustained marketing supportPublishers only invest real marketing dollars in books that are already succeedingHollywood packaging deals often benefit agencies more than the writers themselvesComplete projects teach more than abandoned ones - finish what you startTraditional publishing success requires constant self-advocacy and hustleFamily reactions to memoirs can be complicated, especially around professional jealousy

Hannah Sward’s publishing journey reads like a masterclass in persistence meets divine intervention.After years of writing short stories for underground literary journals, she stumbled into a free writer’s group at a library—complete with homeless people sleeping on the sidelines.That’s where she met Jill Sherry Robinson, an 80-year-old bestselling author who essentially kidnapped her and mentored her until she finished her book.Through a comedy of errors involving three different agents (one retired three months after signing her), Sward eventually sold her book for a whopping $500 advance.But here's the kicker: by the time her book Strip came out in 2022, Sward had built such authentic relationships in the recovery community that the book found its audience organically. No Instagram strategy needed—just good old-fashioned showing up. Now she's chronicling her sexual adventures after 50 on Substack, where she’s learned that—guess what?—vulnerability pays off when book deals may not.Episode Highlights:How Hannah's 14-year friendship with Anna led to confessing literary jealousy at an AA meetingThe serendipitous connection with 80-year-old mentor Jill Sherry Robinson at a free library writers groupHannah's unconventional memoir structure: 75 short chapters designed for non-readersThe grueling agent search: 100 rejections and three failed agent relationships before going soloPublishing with a small press for a $500 advance while her father was dying in hospiceHow building authentic community relationships over years created organic publicity opportunitiesThe launch of "Summer of Men" Substack about sex after 50 that had readers paying to find out what happens nextWhy Hannah refuses to repeat the traditional publishing process for her next bookKey Takeaways:Jealousy among writers is normal and can be processed healthily through honest conversationMentorship can appear unexpectedly - stay open to guidance from unlikely sourcesPersistence pays off: Hannah's father modeled being "the king of rejection" as a badge of honorCommunity building matters more than platform building for authentic book promotionThe publishing process can be an "integrated experience" when you work through disappointments internallySmall press publishing with low advances can still lead to meaningful success and readershipLeading with credentials (blurbs from Nobel Prize winners) gets manuscripts read, not just good writingWriting partnerships and accountability groups sustain creative work over yearsSuccess doesn't fill the internal "hole" - there will always be compare and despair momentsSometimes the journey to publication teaches more than the publication itself

if you’re a subscriber, hi! It’s been a minute. And by a minute I mean it’s been almost a year.That’s because one of the main reasons I do a podcast is so that I can educate myself and after hundreds of interviews, I felt like I’d learned everything I could about how to build authority with a book. I even used many of those interviews in the book I published in 2023, also called On Good Authority.I was surprised to discover that despite not posting any new episodes, this podcast has been kicking along—remaining in the top 1% of podcasts just because new people are finding the show, or some of you authority junkies are listening to episodes over and over?Anyway, lately, I’ve been feeling that podcast itch again: that craving for the mic. And I also started a Substack that I’ve loved writing. One day recently it occurred to me that the Substack could have an accompanying podcast and then it occurred to me, hey I already have a podcast – it’s just been lying dormant. And so I’ve renamed the show Behind the Book Cover, same name as my Substack.Now I’m going to be focusing less on how to build authority from a book and more on the past, present and future of book publishing, as I see it.The past is the traditional publishing model, which means I’m going to spend the first season talking to authors who come from that world. We’re going to dive into the things no one wants to talk about: the tough days that follow getting the book deal.Season two will focus on the present: entrepreneurs that are earning literal millions as a result of their books, and how they’re doing it.And season three will delve into where book publishing is going, with a special focus, of course on AI.So why am I passionate about this new direction now? I’m so glad you asked!The Penguin Random House trial in 2023 revealed a lot that had previously been secret—namely, that 85% of book advances never earn out and Random House got its name because, as the CEO said in the trial, they never know which books will succeed so it’s random!The reality is that most authors make less than minimum wage. And here's the kicker—the entrepreneurs who get caught up in these publishing fantasies often end up worse off than when they started. They're so focused on impressing agents and publishers that they forget their actual goal: growing their business.So I'm going to be talking to authors about why traditional publishing dreams often backfire for business owners. I'll introduce you to smart entrepreneurs who use books strategically—not as lottery tickets, but as lead generation machines and authority builders. And I'll expose what the publishing industry doesn't want you to know about how this business actually works.Think of this as the same as On Good Authority but with a sharper edge. Depending on when you’re hearing this, I’ve either already released or am weeks away from releasing the show you know and love but fine tuned for your success. Same juicy interviews, same truth-telling, just more focused on what actually moves the needle in your business instead of feeding publishing fantasies that lead to disappointment.Whether you're thinking about writing a book, struggling with your first one, or wondering if any of this makes business sense, these conversations will save you time, money and heartache.Because here's the thing: once you stop chasing publishing validation and start using books as the business tools they actually are, everything changes. And I can't wait to show you how.Welcome to Behind the Book Cover.

Hilary Lifton is not one to boast, and I write that with more understatement than you can imagine.I was introduced to her recently at a party by someone who said she was a big ghostwriter. When I asked her about her career, she mentioned working on a self-help book.It was only when I Googled her later that I learned she has written 16 New York Times bestsellers and is one of the most sought-after ghostwriters alive. (While she chooses not to name her bold-faced clients, you can find out who some of them are by going to her site.)I've never had such an interesting conversation about ghostwriting and I challenge you that you've probably not heard one. I know that's setting expectations quite high but I'm ready to meet them!

Arlina Allen is a force in the recovery movement. Sober for over 30 years, she's been releasing episodes of her top 1% podcast, ODAAT Chat, for over eight.She's also been working on a book for almost that long—and now it's finally here! The 12-Step Guide for Skeptics: Clearing Up Common Misconceptions of A path to Sobriety is out now and for it, she showed her book-in-progress to people who not only didn't agree with what she was writing but who actually disagreed.In this episode, we talked about her process, how she realized that her original idea for the book was more an article than a book and the way her podcast set her up for book sucess. 

Dr. Douglas Brackmann isn't like anyone else you meet. He's far more intense and brilliant—the kind of person you find yourself telling your deepest and darkest secrets to when you had just planned to ask him about the weather.The author of Driven: Understanding and Harnessing the Genetic Gifts Shared by Entrepreneurs, Navy SEALs, Pro Athletes, and Maybe YOU, Brackmann is revered among top entrepreneurs. And while he admits that he already had "disciples" before publishing Driven, the book still radically transformed his practice, career and life.\Although the tips he provides about building authority with a book are priceless, I was even more intrigued. by how much credibility he says the book has given him (even though he already has two PhDs!) Listen and get inspired. And if you relate to what he says about being a driven person...A) I feel your pain and B) there are many ways to work with Brackmann on that. Find out what they are by going here.(BTW: I was on his podcast a few months ago. You can hear that here.)

Erika Ayers Badan calls herself a “token CEO”, the rare female employee in the highest rank of a bro-roar sports and new media culture—specifically, at Barstool Sports, which she took from a rough-and-tumble sports and betting brand and turned it into a $550 million juggernaut with more than 5 billion monthly video views and 225 million followers. In her book, Nobody Cares About Your Career: Why Failure Is Good, The Great Ones Play Hurt, and Other Hard Truths, she talks about all that and more. And in this podcast episode, she discusses why she decided to do a book at this point in her career, how it serves as a “receipt” for what she’s done and how she truly doesn’t give an f what other people think.

It’s truly a crime that there’s no TV series about Jill Ishkanian.The lone female tabloid reporter in a sea of men, Ishkanian has been raided by the FBI, exonerated Meghan Markle and been late to a lunch date with me because she thought she saw Kevin Costner driving. And those are just three of dozens of fascinating facts!Yet, despite the fact that she’s been technically employed as a writer for decades and knows she has a hell of a story to tell, she’s been stalled on writing her book. Why is that? And how can we—yes, the collective we—help her? It’s all in this episode.

While Mark Gottlieb has agenting in his blood—he’s a second generation lit agent—he’s not your typical agent. He doesn’t specialize in any particular genre but bounces between fiction and nonfiction, with some children's books and graphic novels in between. And though he works with the Big Five publishers, he’s open-minded when it comes to self-publishing and the new wave of publishing. In this episode we talked about how being a writer requires audacity, how tough it is to make a living as an author without a side profession and how most people don’t even know what a lit agent is, among many other topics. 

Here's a special release for you: the keynote I recently gave at a mastermind that encompasses so much of what I know to be true about coming up with your book idea. It's short but sweet. Enjoy!FOR MORE ABOUT THE PODCAST AND OTHER STUFF, GO TO WWW.ONGOODAUTHORITYPOD.COM.