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How I’d start a writing business (If I started over)

Published 3 days ago • 3 min read

Hi Reader,

I started my writing business back in 2014.

As your internet elder, I’m here to report that 2014 was a simpler time.

TikTok hadn’t wrecked the internet, and our attention spans back then with short-form content.

Elon spent his days building SolarCity and not trolling the woke left on X.

And my inbox wasn’t stuffed full of pitches for AI “developers” hawking a ChatGPT port and overpromising cha-ching affiliate commissions.

In 2014…

My writing blog was a fun side project.

I wrote blog posts and tinkered with SEO tools before my day job.

I also worked as an in-house copywriter for a SaaS company.

For my day job, I wrote about why business owners should ditch Microsoft Excel for accounting software.

Fun times.

(When I started my writing business, I ditched the spreadsheets… for an accountant.)

I learned on the job how to write copy that sells.

Profitable times.

(I’d need those skills later)

I didn’t realize I’d started a writing business until 2016.

I somehow stumbled into the world of display advertising and affiliate marketing.

It didn’t happen at once, but…

Money from my side gig or blog outpaced my salary from my copywriting job.

Even then…

I didn’t march into my boss’s office and declare, “I quit!” until 2020.

I’ve always been the last person to turn up at a party.

Years earlier, I got burnt. I tried to launch a freelance writing career… with no clients, no savings, and no plan.

(Don’t do that)

My writing business model has changed many times since I said, “I quit!”

Earning a living writing in 2024?

Somedays, it feels like I’m fighting in a war for attention.

Mine and my ideal clients.

I sometimes miss working with a big team.

But I could never go back into a hellscape that is a fluorescent-lit glass office.

I’d rather rub lemons in my eyes than spend an afternoon sitting through hours of bland PowerPoint presentations over Microsoft Teams.

If I were starting a writing business today, I’d do three things:

First up…

I’d write a daily newsletter.

In 2014, an email list was the cornerstone of a profitable writing business.

In 2024, an email list IS the cornerstone of a profitable writing business.

I started my first email list with MailChimp.

MailChimp was free, and writers love free things.

Plus, they’d cute monkey branding.

But cute branding wasn’t enough.

I quickly discovered that MailChimp prefers retail businesses and e-commerce stores over lone Irish bloggers.


ConvertKit is better for creators.

They say so on their homepage!

The best way to grow your email list?

Practice in public by writing daily emails.

Writing in public, even if you think no one is reading your work.

You might be surprised.

A while ago, a reader wrote in.

He told me he’d read all my stuff.

He wanted me to know I wasn’t writing into the void.

Pressing publish clarifies your thinking, no matter how small your list or audience is.

It forces you to cement a writing habit.

You’ll need that later.

When a client asks, "What do you write?" point to your back catalogue of published works.

I coached a writer on this strategy a while ago.

They recoiled from the thoughts of writing and sending that many emails.

Does writing a daily newsletter sound like the equivalent of deadlifting your body weight after spending months binging Pizza and Friends on Netflix?

If so, start small.

No need to tear a disc.

Warm up with a weekly newsletter. Like a novice weightlifter racking more plates on the barbell each week, gradually increase your cadence.

The ConvertKit Creator network helps writers grow a list organically without spending money on ads.

You refer them. They refer you. A flywheel, if you will.

That said…

I’d also write online to attract readers and potential clients.

More on that tomorrow.

I’d like to invite you to a Pro Writers Only workshop next week on this topic. How to Start a 6-Figure Newsletter Business. Buy a ticket.

Write on,
Bryan Collins

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My name is Bryan Collins. I'm a content strategist, copywriter and USA-Today best-selling author.

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