Dennis Hensley was the very first real writer I ever knew—back when getting a book published felt like spotting a unicorn in 1990s LA.

His debut novel Misadventures in the (213) came out in 1998, and I thought it was the coolest thing imaginable.

Years later, we'd find ourselves sweating through Ben Allen's dance classes together, proving that creative people really do wear all the hats.

Dennis has written for everyone from Joan Rivers to Wondery podcasts, created party games and somehow made more money dancing in commercials than writing this year.

Our conversation (recorded the day before his 61st birthday) goes deep on resilience, disappointment and figuring out how to keep creating when the scoreboard stops making sense.

Topics Discussed:

• The 1990s writing gold rush: When Gen X believed you could actually make a living as a writer, gift bags overflowed at parties. and  magazines paid $1 per word
• Breaking in: How an audition rejection for Madonna's Blonde Ambition tour became Dennis's first published article, leading to gigs at Movieline, Detour and beyond
• Writing for free (for three years): The unglamorous hustle behind Misadventures in the (213), including interviewing Carrie Fisher in her bed and scoring a gym membership through barter
•  The 2013 Fashion Police strike: How standing up for freelance writers' pay during the Writers Guild organizing effort traumatized Dennis, cost him his best friend/roommate and triggered a health crisis that changed everything
• Rehab for disappointment: Dennis's raw account of hospitalization, thinking he'd "die of disappointment" and the long road through somatic therapy, meditation and redefining success
• Changing how you keep score: Why tracking wins vs. losses will destroy you, and how Dennis learned to measure creative life by "who I'm being" rather than what he's getting
• The game that almost was: Pitching "You Don't Know My Life!" to Jason Bateman's production company, feeling good about the pitches, getting rejected—and being sad for only five seconds
• "Everything is impossible, so anything is possible": Life lessons from artist Stephanie Elizondo Griest and why trying matters more than outcomes
• Dancing pays better than writing: How Dennis made more money this year from Vegas commercials than his writing career, and why he's okay with that

Mentioned:

• Misadventures in the (213) and Screening Party books
• Rob Weisbach, Detour, Movieline, Fashion Police
• "You Don't Know My Life!" party game
• Podcasts: Dennis, Anyone? and Dennis Hensley's Happy and Gay
• Ben Allen's Group Three dance class (RIP the Thriller flash mob)

Heather Wood Rudulph has done many things in the publishing world, including co-writing Sexy Feminism: A Girl's Guide to Love, Success and Style with Jennifer Keishin Armstrong (a title that very much captured a specific moment in feminist evolution but makes Rudulph give a tiny cringe now).

We met back in the New York media heyday when things like "readings and rub downs" (yes, book readings with massages) seemed totally normal.

Heather's spent over a decade writing about culture and entertainment for everyone from Cosmo to Rolling Stone and now wears many hats in the words world (including as an occasional editor for my company!) This conversation digs into the realities of traditional publishing: the battles you pick, the dreams that get dashed and why understanding business matters as much as loving words.

Topics Discussed:

• Fighting for your title: How Heather and her co-author battled their publisher five times to keep Sexy Feminism as their title and why picking your battles matters when you have so little control
• The subtitle that aged: Why A Girl's Guide to Love, Success and Style captures a specific moment in feminist history that "wasn't quite there yet"
• Traditional publishing reality check: Self-funded book tours, throwing yourself parties in cities where you have friends and learning that you're essentially your own PR machine
• The $0 royalty statement: Getting trolled by emails showing zero earnings, letters about books being destroyed in landfills and the occasional thrill of foreign translations
• "You're lucky to be publishing a book": Why authors have to make compromises to get to the finish line but also when to stand firm
• The proposals that break your heart: Six months developing a Madonna book pitch, not getting the deal, watching someone else write basically the same book
• Writers don't get paid for proposals: The reality that you don't earn anything for pitching articles, writing proposals or preparing to teach—only for the finished product
• When the golden curtain opens: Jennifer Keishin Armstrong's revelation that publishers only hold real marketing meetings after you've proven you're successful (her Seinfeld book hitting the NYT list)
• The advance is not vacation money: Why even six-figure book deals aren't what people think and how writers should already be thinking about the next book before the first one comes out
• From entertainment reporter to marketing: How Heather pivoted from writing fluffy celebrity profiles and traveling to spas worldwide to understanding that storytelling lives in business too
• The entrepreneurship of writing: Why understanding business isn't selling out—it's survival and how freelancers have to become their own marketing departments
• Amazon is the list that matters: Not the New York Times bestseller list but Amazon rankings and reviews from regular people that live forever
• "Anybody can write a book": But it's like running a marathon—you have to train, know what you're getting into, keep going when it hurts and want it for the right reasons

Mentioned:

• Sexy Feminism: A Girl's Guide to Love, Success and Style
• Jennifer Keishin Armstrong (co-author and TV show book specialist)
• SexyFeminist.com (their website that became the book)
• The era of Feministing and Jezebel
• "Readings and Rub Downs" events at Birch Coffee
• Work at Cosmo, DAYSPA magazine, LA Daily News and various digital media companies
• The sustainability startup that paid $2/word (briefly)
• Launch Pad Publishing (Anna's company where Heather now occasionally freelances)

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 overnight
• The strategic decision to write a proposal instead of submitting a completed manuscript
• Why Jeanne chose Riverhead and editor Sarah McGrath over the highest bidder
• The simultaneous media blitz: book launch, Vogue excerpt, and This American Life feature
• How HBO optioned the book before publication, leading to pilot writing opportunities
• The 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 presses
• Why she's returning to grassroots theater after a decade in Hollywood
• The father-daughter dynamic when children outachieve their parents professionally

Key Takeaways:

• Two years of persistence can lead to overnight success 
• Agents and gatekeepers are "smart secretaries" - you must drive your own career
• Women wait 8 months to resubmit after rejection; men wait 3 days
• Big advances don't guarantee book tours or sustained marketing support
• Publishers only invest real marketing dollars in books that are already succeeding
• Hollywood packaging deals often benefit agencies more than the writers themselves
• Complete projects teach more than abandoned ones - finish what you start
• Traditional publishing success requires constant self-advocacy and hustle
• Family 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 meeting
• The serendipitous connection with 80-year-old mentor Jill Sherry Robinson at a free library writers group
• Hannah's unconventional memoir structure: 75 short chapters designed for non-readers
• The grueling agent search: 100 rejections and three failed agent relationships before going solo
• Publishing with a small press for a $500 advance while her father was dying in hospice
• How building authentic community relationships over years created organic publicity opportunities
• The launch of "Summer of Men" Substack about sex after 50 that had readers paying to find out what happens next
• Why Hannah refuses to repeat the traditional publishing process for her next book

Key Takeaways:

• Jealousy among writers is normal and can be processed healthily through honest conversation
• Mentorship can appear unexpectedly - stay open to guidance from unlikely sources
• Persistence pays off: Hannah's father modeled being "the king of rejection" as a badge of honor
• Community building matters more than platform building for authentic book promotion
• The publishing process can be an "integrated experience" when you work through disappointments internally
• Small press publishing with low advances can still lead to meaningful success and readership
• Leading with credentials (blurbs from Nobel Prize winners) gets manuscripts read, not just good writing
• Writing partnerships and accountability groups sustain creative work over years
• Success doesn't fill the internal "hole" - there will always be compare and despair moments
• Sometimes 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.