The Writer's Round

The Writer's Round

By Kendall CherryBusinessEntrepreneurship
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The Writer's Round episodes

  • Why Most Writers Suck at Marketing Their Services

    If you feel like you “suck at marketing,” you probably don’t. 

    In this episode, I make the case that most writers (and founder-writers) have a sales messaging problem, not a marketing problem—and I unpack the deeper story that keeps you stuck: the starving-artist narrative.

    Here’s what we cover:

    • Why marketing is the speaker, but sales messaging is the song.
    • How “my marketing isn’t working” often means “my message isn’t selling.”
    • The real block: fear of selling, not lack of platforms or posts.
    • How the starving-artist narrative sneaks into your pricing and positioning.
    • Everyday examples of that narrative in media—and why it’s so seductive.
    • Why rejecting that script is step one to consistent revenue.
    • How expanders (living or dead) rewire what you believe is possible.
    • A simple first move: pick a platform, fix the message, and sell clearly.

    If you’re ready to stop hiding behind “more content” and start saying the right thing, this one is tough-love with a compass.

    CONNECT WITH KENDALL:

    👩🏼‍🌾 Applications are OPEN for the inaugural cohort of The Greenhouse 🌱🌻 a 6-month accelerator to grow your writing business and transform your words into a premium product

    Website: candidcollective.co

    LinkedIn: https://www.linkedin.com/in/kendall-cherry/

    Subscribe to my newsletter, Wallflower Fridays 🌻 💌 wallflowerfridays.com

    The Writer's Round on Substack: thewritersround.com

    PREMIUM SUPPORT

    Join The Greenhouse 🌱🌻 A 6-month accelerator to grow your writing business and transform your words into a premium product that clients love to pay you for. Apply here: findthegreenhouse.com

    Want to hire me to write for you? 👻✏️ Grab my services guide: candidcollective.co/services-guide

    © The Candid Collective

    34 min
  • Is AI Really Going to Replace You as a Writer?

    Is AI actually coming for your writing career—or are we confusing speed with substance? 

    In this episode, I cut through the hype to show what AI does well, where it falls flat, and how you can future-proof your craft and income.

    Here’s what we cover:

    • Why AI outputs the average—and why differentiation wins.
    • How a human voice drives retention, resonance, and conversion.
    • The tell: converting content is rarely AI-generated.
    • What my clients say they want from human-written work.
    • Sales writing vs. low-value content—and the 2026 reality check.
    • The shift to decentralized work and contractor-led teams.
    • The printing press analogy: tools scale volume; humans scale meaning.
    • How I use AI to offload busywork, not my core voice.
    • Why “AI-powered” soon won’t be a selling point.
    • Concrete next steps to protect and grow your writing income.

    Whether you’re a ghostwriter, founder-writer, or creator, you’ll leave with a clear plan: double down on distinct voice and sales skills, use AI strategically, and build a writing business that lasts.

    CONNECT WITH KENDALL:

    👩🏼‍🌾 Applications are OPEN for the inaugural cohort of The Greenhouse 🌱🌻 a 6-month accelerator to grow your writing business and transform your words into a premium product

    Website: candidcollective.co

    LinkedIn: https://www.linkedin.com/in/kendall-cherry/

    Subscribe to my newsletter, Wallflower Fridays 🌻 💌 wallflowerfridays.com

    The Writer's Round on Substack: thewritersround.com

    PREMIUM SUPPORT

    Join The Greenhouse 🌱🌻 A 6-month accelerator to grow your writing business and transform your words into a premium product that clients love to pay you for. Apply here: findthegreenhouse.com

    Want to hire me to write for you? 👻✏️ Grab my services guide: candidcollective.co/services-guide

    © The Candid Collective

    44 min
  • What I’ve Learned in 4 Years of My Ghostwriting Business

    What does it really take to run a ghostwriting business—and keep it thriving—in today’s shifting creative economy? 

    In this episode, I share the lessons, pivots, and hard-won insights from four years of building The Candid Collective® and serving clients at every stage of growth.

    You’ll hear the raw truths about money, clients, content, and resilience, along with encouragement for any writer or entrepreneur carving their own path.

    Here’s what we cover:

    • How I accidentally became a ghostwriter during the pandemic.
    • Why retainer clients and content libraries create stability and freedom.
    • The difference between ghostwriting and generic content writing.
    • How storytelling and sales writing blur into a powerful business asset.
    • Why writing from a personal brand converts better than faceless company posts.
    • How to think about AI, low-value content, and the future of the industry.
    • Lessons in leverage: money, risk, and investing in the right support.
    • Why the best brands still pay top dollar for authentic, human ghostwriting.

    If you’ve ever wondered what it takes to build a creative business that lasts—or how to future-proof your writing career—this episode gives you a candid behind-the-scenes look at what works, what doesn’t, and what’s next.

    CONNECT WITH KENDALL:

    👩🏼‍🌾 Applications are OPEN for the inaugural cohort of The Greenhouse 🌱🌻 a 6-month accelerator to grow your writing business and transform your words into a premium product

    Website: candidcollective.co

    LinkedIn: https://www.linkedin.com/in/kendall-cherry/

    Subscribe to my newsletter, Wallflower Fridays 🌻 💌 wallflowerfridays.com

    The Writer's Round on Substack: thewritersround.com

    PREMIUM SUPPORT

    Join The Greenhouse 🌱🌻 A 6-month accelerator to grow your writing business and transform your words into a premium product that clients love to pay you for. Apply here: findthegreenhouse.com

    Want to hire me to write for you? 👻✏️ Grab my services guide: candidcollective.co/services-guide

    © The Candid Collective

    1 hr 10 min
  • Welcome to The Writer's Round

    Ever wish there were a corner of the internet where writers are treated like artists and business owners—without fear-mongering about AI or hustle-bro marketing? This inaugural episode sets the tone for The Writer’s Round: a candid, unvarnished, “guitar-and-a-mic” space for craft, career, and creative sovereignty.

    Rather than promising a one-size-fits-all blueprint, I'll offer an honest, practical look at building a writing life in 2025—where business is art, art is business, and your voice belongs at the table.

    Here’s what we cover:

    • Why this show exists as an antidote to scarcity and performative “authority.”
    • My path from corporate comms to The Candid Collective® and book writing.
    • How resourcing yourself (team, coaching, systems) strengthens art and business.
    • The Nashville writer’s round as a model: no hierarchy, just respect for craft.
    • Why creative control and IP ownership led to founding Lyora Ink.
    • What to expect: batched drops every two weeks, raw and minimally produced.
    • Who it’s for: ghostwriters, copywriters, founder-writers, and working artists.
    • How to participate: send questions and ideas to [email protected]

    Whether you write to sell, to teach, or to tell the truth, this episode welcomes you into a round where your story—and your sovereignty—matter.

    CONNECT WITH KENDALL:

    👩🏼‍🌾 Applications are OPEN for the inaugural cohort of The Greenhouse 🌱🌻 a 6-month accelerator to grow your writing business and transform your words into a premium product

    Website: candidcollective.co

    LinkedIn: https://www.linkedin.com/in/kendall-cherry/

    Subscribe to my newsletter, Wallflower Fridays 🌻 💌 wallflowerfridays.com

    The Writer's Round on Substack: thewritersround.com

    PREMIUM SUPPORT

    Join The Greenhouse 🌱🌻 A 6-month accelerator to grow your writing business and transform your words into a premium product that clients love to pay you for. Apply here: findthegreenhouse.com

    Want to hire me to write for you? 👻✏️ Grab my services guide: candidcollective.co/services-guide

    © The Candid Collective

    44 min

About The Writer's Round

From the publisher's feed

A creative sanctuary for writers, business owners, and artists who are called to stay gold in this brave new world