Calvin Bagley spent his childhood dodging the school bus and adulthood building business empires. The founder of multiple eight-figure Medicare companies and a self-proclaimed “big fish in a very specific pond,” Calvin went from growing up in rural isolation with nine siblings and no formal schooling to becoming one of the most respected names in his industry.

His memoir Hiding from the School Bus doesn’t teach you how to scale a business—it shows you how to survive one hell of a childhood and still come out kind, successful and grateful.

In this episode, Calvin and I cover everything from family feuds to Kirkus raves to what it’s like when people you barely know suddenly know all your darkest secrets. He talks about writing 1,000 pages during a bout of shingles (because of course he did), taking his co-writer back to the “scene of the crime” to really feel the trauma and throwing a Vegas book launch complete with goats, carrot cake and cocktails named after his childhood pain.

It’s equal parts therapy session, comeback story and gratitude circle. Calvin somehow manages to turn abuse, neglect and educational deprivation into punchlines—and then pivots to heartfelt lessons on self-acceptance, fatherhood and what it means to finally stop running from your past.

Episode Highlights

• What happens when your mom doesn’t know you wrote a memoir
• How a shingles outbreak became a literary blessing (seriously)
• The Vegas book party that doubled as emotional closure
• How radical honesty can make your business stronger
• What happens when you tell your story and the world actually listens

Ethlie Ann Vare has lived through every incarnation of the media machine—from the era when editors and agents were true gatekeepers to today’s age of algorithms and the “wisdom of the crowd.” A journalist, TV writer and author, Vare built a career on talent, timing and serendipity. She went from covering rock shows in 1980s Los Angeles to penning biographies of Stevie Nicks and Ozzy Osbourne then spent 15 years writing for television shows like Renegade, Silk Stalkings, Andromeda and CSI.

In this episode, Vare reflects on how the publishing world she once knew—where publicists flew authors to The Today Show and books stayed in print for decades—has vanished, replaced by a firehose of content and a marketplace where visibility often trumps talent. She laments that authors are now the product, forced to become their own marketers and brands while readers drown in choice.

A savvy observer of both life and the publishing industry, Vare has proven that good work finds its way. Her New York Times–noted Mothers of Invention and later Love Addict: Sex, Romance and Other Dangerous Drugs (which began as a Tumblr called Affection Deficit Disorder) both emerged from two respective subjects she cared deeply about—women inventors and the psychology of love addiction. Now through her Substack of the same name ,she continues to write “for fun and for free,” offering hard-earned wisdom without worrying about the clicks or sales.

Episode Highlights:

• Ethlie recounts her early days in rock journalism where being “good and lucky” opened doors to Billboard, Rock Magazine and national TV appearances.
• The shift from gatekeepers to algorithms: how the fall of traditional publishing replaced discernment with popularity contests.
• Behind the making of her hit book Mothers of Invention and why its success led to a national lecture tour and lasting influence.
• Her perspective on today’s “firehose of content,” author branding and the exhaustion of self-promotion.
• The origin of Love Addict, her dive into sex and love addiction and how it evolved from personal exploration to public service.
• Reflections on age, authenticity and the strange liberation of being a “digital immigrant” in a youth-driven culture.

Key Takeaways:

• The creative industry has shifted from talent being discovered to visibility being demanded.
• Writing remains a calling worth pursuing—for love not for money.
• Democratization has come at a cost: fewer filters more noise.
• The real reward of authorship isn’t fame but connection and survival through reinvention.

Jamie Rose is proof that reinvention can be a superpower. After decades as a working actress, she did what most in Hollywood never dare: she pivoted.

First came writing. She landed a Penguin deal for her memoir Shut Up and Dance, diving headfirst into the brutal world of publishing. Then came coaching, where she transformed her 37 years of training with psychiatrist Phil Stutz (of The Tools and Jonah Hill’s Netflix doc Stutz) into a career helping others unlock their potential.

Now she’s tackling her boldest project yet: Facing Madame X: An Initiation into Feminine Power (out March 2026). Part memoir, part self-help, the book distills Stutz’s groundbreaking tools through Jamie’s uniquely female perspective, weaving hard-won lessons of resilience, humor and creativity.

Jamie had to figure out the system for herself. She rode the highs (landing a book deal with a major publisher) and the lows (refreshing Amazon rankings until she nearly lost her mind). She discovered that success wasn’t about fame or money alone—it was about emotional “f-you money,” joy in the process and leaving a legacy that makes people weep (in the best way).

Episode Highlights

• Jamie’s leap from Hollywood (Falcon Crest, The Tonight Show) to published author and coach
• The rollercoaster of her first book Shut Up and Dance—Penguin deal, PR mishaps, Amazon obsession
• Lessons from 37 years with mentor Phil Stutz, now shaping her new book Facing Madame X (2026)
• Redefining “f-you money” as emotional freedom, not just financial security
• Why reinvention, resilience, and joy matter more than chasing external validation

Key Takeaways

• Traditional publishing offers prestige but little control—authors must drive their own success
• Setbacks can spark reinvention and deeper purpose
• Mentorship and long-term practice transform both work and life
• Emotional wealth and detachment create true power
• Books are about legacy and impact, not just sales numbers

Mark Ebner has lived every journalist’s dream. He’s a New York Times bestselling author, Hollywood insider and the guy behind some of the most notorious exposés in entertainment history. But behind the bylines and book deals is a story about an industry that chews up even its most fearless voices—and a writer who found a way to keep telling the truth anyway.

In this conversation, Mark and I talk about everything the publishing world doesn’t want you to know—from missing royalty checks and botched releases to what happens when AI starts scraping your life’s work. He opens up about his unlikely friendship with Andrew Breitbart, the chaos of the book business and how he went from bestselling author to private investigator—while somehow staying one of the funniest, most unflinchingly honest people I’ve ever met.

Episode Highlights

• The truth about what it really means to hit the New York Times list (and why it doesn’t make you rich)
• How HarperCollins mishandled his biggest book deal—and what it taught him about the industry’s dysfunction
• The unexpected camaraderie between a radical leftist and a far-right pundit and how it produced Hollywood, Interrupted
• Why bookstores literally killed one of his bestsellers by shelving it in the wrong section
• The burnout and betrayal that pushed him to leave journalism and launch a private investigation firm
• His take on AI, intellectual theft and the future (or end) of nonfiction writing
• The celebrity scandals, lawsuits and cult investigations that defined his career—and why he’s done telling other people’s stories
• The strange parallels between chasing leads as a PI and chasing truth as a reporter
• The book he still wants to write—and why he might call it Dirtbag

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)

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