How I Started A $10K/Month Subscription-Based Copywriting Service

Published: January 10th, 2023
Milly Barker-DeStefano
Founder, heylexi
from Wallingford, CT, USA
started November 2022
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Note: This business is no longer running. It was started in 2022 and ended in 2023. Reason for closure: Acquired.

Hello! Who are you and what business did you start?

Hey hey! My name is Milly Barker-DeStefano and I am the founder of heylexi, a productized service offering publish-ready copy and content on a flexible and scalable monthly subscription.

I’ve been a part-time freelance writer since I was 14 years old (one of my first clients back then was eBay, believe it or not!) and after experiencing the frustrations and aggravations of hiring freelance writers for my projects, I decided to take a closer look at how businesses acquire their copy and content.

What I found was a pretty horrendous process (more on that later), so I set about to create something better.

My resulting flagship service is heylexi Standard, which gives you unlimited copy and content requests, unlimited revisions and rewrites, unlimited team members, a 48-hour turnaround Monday-Friday, an SEO package (primary keyword, slug, SEO title, meta description, featured image alt text) with every blog post, premium stock images, and editing and proofreading. That service runs at $2,999 p/m if you’re paying monthly (or $2,499 p/m if paying annually).

For a little extra ($3,999 p/m paid monthly or $3,499 p/m paid annually), you can get heylexi Pro, which includes everything in the Standard plan plus unlimited brands (great for agencies), SEO monitoring and topic ideation, social media collateral for every post, and up to one hour of content, strategy consulting each month.

My clients are growth stage startups that want to take their founding teams off content creation but don’t want the expense of hiring in-house or the hassles of managing freelancers.

I still take on some ad hoc copy and content writing for companies that don’t want the package deal, but that is getting more and more limited as I fill my client book.

heylexi launched in November 2022 and, at the time of writing, is doing around $10k per month. Not bad for a two-week-old service!

The real measure of success for me, however, is the freedom this business model provides. The fact that on a Monday morning, I can be strolling down the beach with my partner and dogs on an extended weekend trip to Martha’s Vineyard, not worrying about workload or schedules or team members…that’s just priceless.


Freelance platforms have become inundated with supply and the result is a race to the bottom on price (which gives you rock-bottom quality as a result).

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

My journey into entrepreneurship is quite unusual in some respects, but I guess it’s interesting!

I’m an international lawyer by training and I enjoyed a successful academic career at the universities of London, Bologna, Harvard, and Oxford during my twenties. I also worked on death row in Louisiana, at the United Nations in New York City, and for a London-based human rights organization where I gathered evidence of soldiers committing sex crimes against children in Liberia. It was tough work, but endlessly motivating.

My north star in that period of my life was delineating the international legal frameworks for humanitarian aid so that more people could get lifesaving assistance in times of disaster. I achieved that when I published my doctoral thesis in 2019.

As rewarding as that work was, however, it doesn’t pay well (though it should). As a result, I had to set up a handful of tiny Internet businesses over those years to be able to pay my bills. I got involved in a lot of things, but the most reliable (financially) was my writing work. I started out writing for content mills at $0.02 a word and soon developed a reputation that now allows me to charge 100x that regularly

Over the past couple of years, I’ve moved out of legal work (apart from some conservation advocacy I do on the side) and have thrown myself entirely into my lifelong passion: entrepreneurship. I’ve tried my hand at a bunch of things and have tested several ideas. I’ve established a personal venture studio to launch and validate ideas quickly, and heylexi is the latest in a series of projects that passed the validation stage and are now in my portfolio.

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

heylexi came about as a confluence of circumstances, but what pushed me to create the service is how terrible it can be trying to hire freelancers as business owners, CMO, etc.

As I mentioned, I’ve run several small companies in the past and whenever I’ve tried to hire freelance writers to help produce copy and content, I’ve always been disappointed.

The thing with copy and content is that you can’t ruy it off the shelf. If you are not doing it yourself (which you shouldn’t be doing as a founder), you have to have it done for you.

The problem is that finding a reliable writer with the requisite skills and industry knowledge is getting harder and harder. Freelance platforms have become inundated with supply and the result is a race to the bottom on price (which gives you rock-bottom quality as a result). Most freelancers are forced to rush work so that they can churn out enough to make ends meet. The ones that don’t are charging prices that most early and growth stage startups simply cannot afford.

And even if you do find a good writer, it’s almost guaranteed that you’ll have to have countless meetings, check-ins, quality reviews, and difficult conversations just to keep quality consistent. Complacency is rife in freelance writing circles, unfortunately.

It was experiencing these kinds of problems first-hand that led me to question what a better way to get copy and content for a business would look like. I concluded that a productized service checks a lot of boxes in this respect:

☑️ Start, stop or pause the service whenever you like

☑️ Fixed, predictable, scalable pricing

☑️ No need to manage workloads or workflows

☑️ Save over 70% compared to hiring someone in-house

☑️ Consistent, guaranteed, and reliable outputs

So, I scratched my owch and built one!

I’m reying to stay focused on being consistent, reducing my stress levels, and delivering exceptional quality content for my clients.

Describe the process of launching the business.

I’ve launched several projects over the past couple of years, and I stressed myself out way too much each time. I didn’t want to do that again. So, this time, I resolved not to launch once, but to launch and relaunch several times. And I’m not done launching yet!

Accordingly, my launch to-do list looked something like this:

  1. Create and publish an attractive marketing website
  2. Write and share a detailed Medium article about the initial launching ✅
  3. Post about the launch on Twitter
  4. Email a few ‘great fit’ past clients ✅
  5. Submit heylexi to startup directories/lists/forums, etc. 🔁
  6. Share updates about heylexi on the #buildinpublic community on Twitter 🔁

It was a low-key launch for sure, but my focus has been on staying consistent and sharing what I’m up to in a way that’s useful for other founders.

The most interesting part of the launch for me was creating the website. I’m usually pretty quick to throw up a basic landing page and start sharing what I’m doing. But this time, I went through a more extensive and iterative process of wireframing, designing, getting feedback, redesigning, etc. before I published it. I even hired a designer to go over my work and make improvements.

Here’s above-the-fold on my first landing page draft:


And here’s the much more focused final version:


(The typewriter is a custom animation that prints some text on a note in front of the heading, rendering a cool depth effect on the page.)

As for costs, it is quite minimal:

  • Domain - $7 for the first year
  • Webflow with CMS - $29 per month
  • Webflow Designer - $400 one-time
  • Google Workspace - $6 per month
  • Stripe - 2.9% + $0.30 per successful card charge
  • MailerLite - free version
  • Zapier - free version
  • Trello Premium - $121.19 per year
  • Ubersuggest - I got a lifetime deal a while back… I think I paid around $120
  • Premium stock images - $1-3 per image

Very roughly speaking, I’m spending around $50 a month to keep the business ticking over. For every client I bring on, I end up paying between $116-$174 per month in Stripe fees, and I spend up to $30 a month on their premium stock assets.

The only other expense is my time in completing the work!

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

I got my first customer by telling previous clients what I was planning to do. One of them signed up before me launching the service, which was a huge confidence boost.

Since then, I’ve kept a full pipeline of prospective clients through sharing progress on Twitter, direct outreach via email, and my embryonic PR efforts.

Here’s a screenshot of heylexi getting featured in the newsletter:


My very simple plan for attracting and retaining customers in the future is:

  • Long-term: SEO
  • Medium-term: PR
  • Short-term: Cold Email/DMs

I’m sure I’ll test other channels at some point, but what I rant for now is a sustainable and simple marketing plan that I can execute.

No complications, no excuses.

So far, the most important lesson I’ve learned is to keep things manageable as a one-woman agency. I’m saying ‘no’ to a lot of my ideas, and I’m turning down work that isn’t a good fit for the business.

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

heylexi is still brand new, but I’m feeling great about where the business is already.

The business model is highly profitable by default, and that will remain the case even if I hire other writers to help me with the workload.

Being an entrepreneur, I know there is always room for improvement and there’s always more to strive for, but I’m trying to stay focused on being consistent, reducing my stress levels, and delivering exceptional quality content for my clients.

Part of what allows me to do this is how streamlined the business operations are. This is what it looks like when I get a new client:

  1. A website visitor converts to a paid client by buying a subscription to my website.
  2. The payment is processed via Stripe, and I receive a push and email notification.
  3. The new client receives an automatic welcome email confirming their payment and detailing what happens next.
  4. I manually create a new Trello board and Google Drive folder for the client in a couple of clicks using templates I made to speed things up.
  5. I manually invite the client to Trello and Google Drive so they have near-immediate access to everything they need to get started.
  6. The client uploads their content requests and other relevant information (brand guidelines, for example) and I get to work, delivering the first piece back within 48 hours on weekdays.
  7. If the client needs to change their subscription or personal details, they can do so via a custom portal I created on the heylexi website (payments are still handled by Stripe for security).

As it stands, it takes me less than one minute to set up a new client. To make that instantaneous, I just need to build automations for the Trello and Google Drive setups (adding that to my to-do list now!)

Once the client is on the board, the process for delivering work back is also ridiculously simple:

  1. When a client adds a new content request to their ACTIVE REQUEST list in Trello (see screenshot below), it automatically shows up in my to-do list (a custom table view board I created in Trello) with a 48 hour deadline.
  2. The copy or content is written in a Google Doc and added to the Trello card using the default Google Drive integration.
  3. Other relevant assets are appended to the card, like a featured image for a blog post.
  4. Questions and feedback are handled on the card itself, reducing the need for meetings and email. Clients are welcome to add voice notes, Loom recordings, text notes, or anything else they want to the card.
  5. When the work is done, the card is moved into the IN REVIEW list, and work starts on whatever comes next in their CONTENT QUEUE.
  6. The client can review the work whenever they want and move it over to APPROVED when they’re happy. If they want revisions, they just move the card back into the ACTIVE REQUEST list and those are worked on before completing anything else.

Here’s what the content board looks like:


(By the way, if you’re thinking this looks a lot like the board that Brett uses at Designjoy, you’d be spot on! I’ve run productized services for years but took a lot of inspiration from how Brett managed his order queue when I started heylexi. Thanks, Brett!)

As for future goals, I’m setting my initial aspirations based on having a sustainable workload, not on reaching a particular level of revenue. In short, my initial plan is to take on more clients until the workload becomes unmanageable and quality is threatened because of it.

I’m playing it by ear and not stating a firm client limit here because I’ve had clients in the past that pay a retainer just to secure our time, and sometimes they only submit one or two requests each month. If that happens, we might be able to take on more clients, but I’ll cross that bridge when I get to it.

I might want to grow a big business one day, but it probably won’t be with heylexi. And that’s OK! I’m not striving to create the world’s biggest copy and content service, but I do want it to be among the very best. With a limited number of clients, highly efficient operations, and an obsessive focus on quality, we can achieve that.

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

So far, the most important lesson I’ve learned is to keep things manageable. I’m saying ‘no’ to a lot of my ideas, and I’m turning down work that isn’t a good fit for the business.

Sure, I could be firing on all cylinders and trying every marketing channel out there to achieve growth. But that is a level of unfocused franticness that I don’t want in my life right now. Slow, steady, sustainable growth is my M.O. for this one!

What platform/tools do you use for your business?

I like to keep my technology stacks as minimal as possible, so I just stick to:

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

  • Podcast: Jonathan Stark’s Ditching Hourly is an absolute gold mine for solo entrepreneurs, consultants, and those looking for a better way to price their services.
  • Book: Seth Godin’s Purple Cow is probably the most value-packed book you’ll ever read about how to distinguish yourself or your products/services.

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

My number one piece of advice for entrepreneurs is to tackle a problem that you have experienced yourself. It’s tempting to jump on whatever is trending or what seems to be working for other people, but if you haven’t experienced what it’s like to struggle with a particular problem before, you’ll find it extremely difficult to convince anyone (directly or through your marketing) that you are the one to solve it for them.

Where can we go to learn more?