222: How to build a million-dollar writing business without selling your soul (with Kieran Drew)

How to Write for a Living

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222: How to build a million-dollar writing business without selling your soul (with Kieran Drew)

Lessons on quitting the wrong career, growing an audience with stories, and building a brand people trust.

David McIlroy

Aug 17, 2025

Transcript

➡️ Grab my FREE 7-day email course, Substack Launchpad - you’ll get one email a day for 7 days to help build your confidence, consistency, and traction on Substack. Get it here.

Season 2, episode 22 is here!

In this episode, Kieran Drew tells me what it was like to leave dentistry to build a thriving online writing business.

He shares how he went from zero audience to over 280,000+ readers and more than $1.3M in revenue, why storytelling became his most valuable skill, and how he balances depth, reach, and revenue in his work.

We cover everything from selling in a human way to resisting the algorithm’s pull, and why curiosity is his ultimate compass for long-term success.

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What we covered:

The moment Kieran decided to quit dentistry and bet on himself as a writer
How one vulnerable story unlocked an audience and reshaped his approach to content
The trap of “incentive drag” and how to avoid losing your voice to trends and algorithms
A simple structure for selling without losing trust or turning people off
Why brand is a long-term moat in the age of AI and how to build it authentically
The three pillars of his business: reach, relationships, and revenue… and how Kieran balances them
His best advice for anyone who wants to quit their job and build a writing business from scratch

👉 Make sure to subscribe to Kieran’s newsletter before you go!

Go deeper:

What’s next?

I’m ready and waiting to support you in the next stages of your creator journey. Here’s a reminder of how I can help:

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The 1K Daily Writing Challenge: Build a consistent habit by writing 1,000 words daily for 30 days. Along the way, you'll get encouraging video prompts, accountability support, and plenty of inspiration to ignite your creative spark. Nail your rhythm. Find your flow. Transform your writing journey forever.
Substack Basics: A video guide showing you exactly how to: set up your first publications; create polished posts from scratch; share, structure, and schedule effectively; and master Notes, CTAs, and growth levers (bonus section: Going Live on Substack).
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