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