Tom Zoellner has no illusions about fame, sales or the myth of the “life-changing book.” A National Book Critics Circle Award winner and New York Times bestselling author, Zoellner has written nine acclaimed works of nonfiction including Island on Fire: The Revolt that Ended Slavery in the British Empire, which also became a finalist for the Bancroft Prize and the California Book Award. But despite the accolades, he’s learned to see writing not as a climb toward visibility but as a lifelong meditation on curiosity and craft.

In this episode, he and I had a lively debate about such things as whether technology is the death knell of creativity or an amazing opportunity, if one should be writing to build authority or to simply to experience the satisfaction of delving deeply into a topic and even how to pronounce BISAC (not to mention his last name).

We also talk about how I once said a sentence to him summarizing how I feel about book publishing that he quotes back to me all the time.

Tom may be my polar opposite in terms of using a book to strategically advance but I do admire the way he writes, as he says, to add one small spark to the larger fire of human knowledge. Listen in to find where you may lie on the spectrum of creativity and commercialism (and where the two meet).

Episode Highlights:

• Tom recounts his journey from local newspapers in Nebraska to national recognition as an award-winning author.
• The evolution of publishing from thoughtful gatekeeping to chaotic marketing—and why he prefers the old systems where “the rules were known.”
• The strange hazards of traditional publishing, from miscategorized books to tone-deaf cover designs and dismissive editors.
• How his first book, The Heartless Stone, grew out of a broken engagement and a trip to the Central African Republic to investigate the diamond trade.
• His growing frustration with publicity, branding and the myth that every author must be a marketer—and how rejecting that mindset changed his relationship to writing.
• His perspective on authorship as both isolation and immersion—solitary work that still requires a deep engagement with life.

Key Takeaways:

• The best part of writing happens at the keyboard, not on the bestseller list.
• Traditional publishing has lost its certainty but the writer’s task remains the same: contribute something meaningful.
• There’s power in humility, patience and persistence in a field obsessed with visibility.
• A book’s true success isn’t measured in sales or awards but in the moment it adds light to the collective bonfire of ideas.

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)