How Sari Botton Blew Past Gatekeepers to Build a Writing Life on Her Own Terms

Welcome, writers and book lovers. The Bleeders is a podcast about book writing and publishing. Make sure you subscribe to the companion Substack: https://thebleeders.substack.com/welcome

Today’s guest is Sari Botton, writer, editor, and publisher of the Substack hits Oldster and Memoir Land, joining The Bleeders to talk candidly about her unconventional path through publishing, why she ultimately chose ownership, longevity, and creative control over chasing traditional industry validation, and how she built a thriving ecosystem around her work.

In this episode, Sari breaks down what it really takes to build a sustainable writing and publishing career outside the gatekeepers. She shares how she launched bestselling anthologies like Goodbye to All That and Never Can Say Goodbye after being repeatedly told “you can’t do that,” what it was like working at Longreads during a pivotal moment in digital publishing, and why Substack ultimately gave her the freedom she’d been seeking all along. 

We also dig into her debut memoir And You May Find Yourself... and the realities of publishing creative nonfiction, including the emotional and ethical challenges of writing about real people, the importance of blurring and revision, and why small presses—and even self-publishing—can sometimes offer more protection and creative freedom than major publishers. This conversation is a must-listen for writers questioning what success in publishing actually looks like in the creator economy.

Subscribe to Sari’s Substacks Oldster, Memoir Land, and Adventures in "Journalism." Follow her on Instagram @saribotton, and buy your copy of And You May Find Yourself... on Bookshop.org, or wherever books are sold!

The Bleeders is hosted by Courtney Kocak. Follow her on Instagram @courtneykocak and Bluesky @courtneykocak.bsky.social. For more, check out her website courtneykocak.com.

Courtney is teaching some upcoming workshops you might be interested in:

• How to Make 2026 Your Best Writing Year Yet: Manifest Your Writing Goals: https://writingworkshops.com/products/how-to-make-2026-your-best-writing-year-yet-manifest-your-writing-goals-zoom-seminar-with-courtney-kocak
• New Year’s Newsletter & Pitch Party Extravaganza (use code BLEEDERS for $100 off): https://www.courtneykocak.com/store/new-years-newsletter-pitch-party-extravaganza-2026
• How to Build a “Platform” for Writers Who Shudder at the Thought: https://writingworkshops.com/products/how-to-build-a-platform-for-writers-who-shudder-at-the-thought-zoom-seminar
• Start a Newsletter to Supercharge Your Platform, Network and Business: https://writingworkshops.com/products/start-a-newsletter-to-supercharge-your-platform-network-business-zoom-seminar
• Land Big Bylines by Writing for Columns: https://writingworkshops.com/products/land-big-bylines-by-writing-for-columns-zoom-seminar
• So You Want to Start a Podcast?: https://writingworkshops.com/products/start-podcast-workshop-courtney-kocak
• Edit & Elevate: Revision Intensive: https://writingworkshops.com/products/edit-elevate-revision-intensive-zoom-seminar-with-courtney-kocak