How I Started A $80K/Month Content Writing Business

Published: April 23rd, 2020
David Tile
Article-Writing Co
from Toronto, Ontario, Canada
started April 2011
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Hello! Who are you and what business did you start?

My name is David Tile. I own and operate a Content Writing Service, under the banner

We don’t consider ourselves a content marketing firm. But a firm dedicated to the business of writing. Project management offers most often attached to marketing agencies. We work against marketing briefs delivering content on time and under budget.


What's your backstory and how did you come up with the idea?

In 2011, coming out of college, I miserably tried to start a penny auction website. I studied Political Science at University, which had absolutely no bearing on this idea. I knew I wanted to do something entrepreneurial and was consumed by this auction model. I had my own specific mechanics that I thought would make the game a lot more fair for the average consumer. But alas, 6-8 months later, after burning through thousands of dollars trying to get the technology right, I was absolutely nowhere.

I was resigned to not give up, but the mechanics of the auction are critical to the smooth operation of the website and if you can’t get it right you don’t have a business. So I decided to start taking on some freelance writing work, just to get some cash in.

One thing led to another and I started getting some bigger clients with bigger asks. Eventually, I snowballed hiring some writers and copy editors. Turning this thing into a full-time business operation.

Within 6 months we picked up some wicked accounts. I was only 23 years old at the time. We had a contract with to be writing 1000 x 750-word articles each week. 1000!!! They were all due Friday evenings. I can tell you that there were a couple completely sleep-ness Thursday or Friday nights trying to get that all in perfectly.

We were NOT equipped to take on that volume so early on in the company, but we went ahead and made do. The content was good. They paid on time, $40k - $50k / month. Lessons learned here were more impressive than anything you’ll learn in business school.

Doing > Thinking. No matter how perfect/smart you are, market forces are smarter. Dive into the river and figure out how to swim.

Take us through the process of designing, prototyping, and manufacturing your first product.

This is a bit tricky. We are a service business. The entire game for us is customer service. It’s a relatively flat market - i.e. you can access a freelance writer in a number of very convenient ways. However, they are such a brutally fickle bunch.

They are reliable one week, might ghost you the next. Perfect work product delivered on a Tuesday might be complete trash Thursday. This fickle reality is where we provide value.

It is a huge time suck to try and scale a writing team to meet growing customer demands. It is also not especially viable to keep a large team inside your company for flexible needs.

Consider coming to our firm last year needing to write 6000 product descriptions in a 9 week period. We are able to conquer this with relative ease, whereas their marketing department would be up the creek.


Describe the process of launching the business.

Snowball. I just went ahead, literally having no idea what I was doing. Failing into every corner and finding success using pure-play guess and check.

The business has been completely bootstrapped. Never taken a dollar in funding. Never taken a dollar in credit. I didn’t even write a business plan to start. Just pure market validation. If the company is growing, that is a good sign.

Lessons learned, however, are that over time you will hit breaking points where you absolutely need to be writing standard operating procedures. Making strategic investments in technology, marketing, and people. You can only ‘fly by the seat of your pants’ for so long, you’ll break your company if you don’t realize this.

It takes a long time to build and maintain the operating principles that define your business…

For instance, we have always been a remote team. Well semi-remote. I personally have had some office space on and off (mostly on) for the life of the company. And I’ve always enjoyed having employees floating in and out of the office.

This has been our reality for 10 years, it appears that with the current pandemic many will catch up to us. Many pros and cons to both sides of the remote work lifestyle. You lose a lot without face-to-face interaction. So you need to schedule a time for in-person stuff with your team. This could be simple in-office meetings. This could be fun stuff like dinner, etc.

You also need to lean heavily on specific systems. One of the things I’ve found most interesting is that employees used to the traditional way of working in-office find it difficult to come aboard. Your work product is completely naked when you are remote. You can’t stand on the social reality of appearing productive and sharp in office. You are entirely judged on the work product that you put in and out. It can be exhausting when you switch. So we have adjusted our early work product expectations to allow for an adjustment period.

Since launch, what has worked to attract and retain customers?

Honestly, we’re in a weird spot. We have been very successful thus far with a full sales operation. But there is an odd dissonance with our business. Content Marketing and Content Writing are very very similar disciplines, obviously. It’s a business, like many “agency” types, where you have to pick a lane, else you risk boiling the ocean.

I.e. you could make a whole business dedicated to writing product descriptions for eCommerce Stores. You could dedicate the agency entirely to ghostwriting blog articles for Real Estate Agents, etc.

So we picked a lane. Scale and project management for marketing agencies and departments. This is our bread and butter. But that does always compute from the outside. Observers of our brand expect to see a content writing service that is adept at using content marketing to market and grow their business.

For us, we have a full sales operation. We are much keener in selecting the types of businesses that will work nicely for us. This way we can be of most value in the market.

Cashflow management is my number one piece of guidance for entrepreneurs. Know where you sit. Don’t let shitty customers delay payments. And if they do - don’t work with them.

How are you doing today and what does the future look like?

Well, naturally this is an interesting time for every single person on the planet. And every single business. Things have changed and will continue to shift every day.

We’ve definitely seen a slow down with a number of paused accounts. A company that services conferences. An NYC coworking space. A travel company based out of the UK. All having to basically freeze their business activity as a result of COVID-19.

That said, we are still profitable. We are still growing. We are lucky that the work we do demands digital attention. As people become more isolated, they are spending oodles more time online.

Through starting the business, have you learned anything particularly helpful or advantageous?

A ton. Overall philosophies that I’ve honed over 10 years in business for myself. Doing > Thinking. This is pretty much a blanket truth in my view of entrepreneurialism. You simply cannot learn more than just getting your hands dirty and failing into every corner. No matter how perfect/smart you are, market forces are smarter. Dive into the river and figure out how to swim.

The best decision that we’ve made as a company is around billing practices. Generally, we bill everything upfront. For larger volume and more complex accounts, we accrue and bill at month’s end. But we only do this once a solid relationship and trust have been built.

Cashflow management is my number one piece of guidance for entrepreneurs. Know where you sit. Don’t let shitty customers delay payments. And if they do - don’t work with them. We had to learn this the hard way... at least 3 different occasions over ten years in business where we’ve been screwed. Probably close to the sum of $15k.

If they aren’t paying you properly on your terms, they aren’t really your customer. Lose em and find someone better.

What platform/tools do you use for your business?

We are a completely remote company. Rely heavily on...

What have been the most influential books, podcasts, or other resources?

Rocket Fuel. The dynamic duo model of a visionary and an operator is such a smart way to think about smart companies. You need visionaries to see the future that the company can accomplish. And you need the operators to ground that with how do we make that vision happen.

The E-Myth. The biggest takeaway for me here was the notion that you must be writing everything down inside your business. Systems and Processes don’t just help your staff operate the business, these are the business. This is what you are selling in the marketplace. Not the bag of chips, per se, but the process to keep that recipe consistent or the system to keep the price competitive.

Advice for other entrepreneurs who want to get started or are just starting out?

Just f--n do it! Nike was right, haha. I have so many conversations with friends, etc. who are passionate about something, have smart ideas, talk game on how they want to start a biz, etc. But they always get paralyzed. Some of my favorite businesses are the simplest. My dog walker. My barber. Competitive spaces for sure, but tons of local need in a big city like Toronto.

Point is if you can do quality work at the right price. If you can present the quality of customer service you should have a place in the market. The Key is that you just go out and get it done. Most people over-think what it takes to be in business. They are scared and put the whole notion on a massive pedestal.

Are you looking to hire for certain positions right now?

Writers & Business Development Reps. We have a strong system in place to onboard junior writers and turn them into copy/content writing pros. And we have a strong sales operation, with big-no-cap incentives for our best salespeople.

Where can we go to learn more?