We're Using Our Agency Experience To Build A Paid Newsletter

Published: September 27th, 2021
Joseph Solomon
We Do It Remotely
from Toronto, ON, Canada
started April 2018
Discover what tools Joseph recommends to grow your business!
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Discover what books Joseph recommends to grow your business!
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Note: This business is no longer running. It was started in 2018 and ended in 2023. Reason for closure: Shut down.

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

My name is Joseph Solomon, and I’m the Founder & CEO of We Do It Remotely.

WDIR is currently a side project that started as a content agency writing high-converting content for businesses in the eCommerce space. We took our knowledge of landing high-paying clients and turned it into a premium course. This course was a 4-week training program that took freelancers through stages of building a portfolio, crafting compelling pitches, and setting up work contracts with clients. It generated $500-2500 a month.

One of our main focuses now is reaching a wider audience through our newsletter. In this newsletter, we share actionable tips and insights to freelancers worldwide who want to grow their remote freelance businesses. Most of the freelancers we serve are writers and marketers, but we’re trying to help freelancers in other industries succeed by applying key concepts to their client search. Most of our course students came from referrals and our friends working full-time jobs but wanting to build side hustles.

The newsletter launched last month but is growing quickly. We recently launched a paid section where we do deep dives into proposals, share exclusive freelancing reports, and more actionable strategies to help freelancers win.


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

I first heard the term location independent in 2015. At the time, I had a crappy job in an industry I didn’t like and was looking for my next step. I started a blog on the side that picked up traction and helped me land my first content management job. Through my gained experience, I started offering freelance writing services and quickly built a roster of quality clients. I took my freelance business on the road and never stopped traveling.

It’s important to be courageous. This means launching even if you’re scared or feel that you’re not ready. You never know what you’re capable of building. You learn so much by doing and making mistakes along the way. These “mistakes” eventually set you up for success.

I learned a lot over the years and have had my fair share of problems. I’ve dealt with losing 6-figure contracts, firing crappy clients, having payment withheld, and much more. Freelancing is freeing but it isn’t all beaches and adventure. It requires a high level of discipline, proactivity, and energy.

Over the last four years, I’ve crossed off bucket list destinations, had incredible experiences, and met unforgettable people along the way. I’m living a more vibrant, fuller life through my freelance and remote work. I’ve been able to pour more into my relationships, build healthier habits, and generally grow as a person. This passion for living life fully is what led to the creation of WDIR.

Secondly, a lot of the information on freelancing is either too vague or just regurgitated from outdated sources and the like. My team and I put together the Freelance Wins newsletter because there’s a lack of powerful, actionable freelance advice by freelancers for freelancers.

Take us through the process of turning your agency experience into a newsletter.

The first thing we were doing was offering copywriting and content marketing services to eCommerce businesses.

This happened pretty organically through connections and client referrals. For our four-week course, leads came in from our friends and network. We put up a small message on Instagram with a call to action to our audience to DM us. The first post got about 100 or so likes, several comments, but more importantly, got 10 DMs. We closed 3 out of 10 students in our first go.

Our first student for the course was a friend who worked full-time as a marketing analyst and wanted to start freelancing on the side.

The newsletter, our newest product, is a simple Carrd, Twitter, and Revue stack. We set up a landing page using Carrd and connected the email form to the Newsletter tool Revue. We use Twitter to build our audience and connect organically with other freelancers. The free newsletter is growing and we’re building an engaged following. Our focus over the next six months is to hit $1,000 MRR for our paid newsletter.


Describe the process of launching the business.

Everything we’ve been doing has been self-funded. We’re big believers in bootstrapping and doing more with less. This doesn’t mean we’re closed off to venture capital or other forms of funding as they can accelerate growth. For the moment, self-funding WDIR is going well.

A big lesson I learned is to launch and then adjust.

A big lesson I learned is to launch and then adjust. This is an excellent exercise in having a bias towards action and getting things in front of potential customers as fast as possible. Another lesson is to lead with value. We’re committed to creating one of the best resources for freelancers around. This means consistently putting out good content and making sure that we’re giving our audience an actionable takeaway. We do everything to empower freelancers.

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

Our Freelance Wins Newsletter has grown mostly from Twitter. We’re participating in weekly chats, doing threads, retweeting, and liking tweets.



We’re also using places like Indiehackers and Reddit to share our growth and be part of organic communities.


We’re exploring partnerships with innovative companies in the Remote Work/ Digital Nomad/ Future of Workspace. Of course, we’re always open to partnerships with other freelancers or freelance platforms. There’s so much opportunity for collaboration in Freelancing!

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

Our paid newsletter is the first of a couple of subscription ideas we’re envisioning. We are building a library of courses and products intending to empower freelancers. More of that is to come over the next couple of years.

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

Being disciplined is key in launching any kind of business, especially a newsletter. You’ve got to put out great consistently and set hard deadlines for yourself to get things done. One of the best ways to build good habits is environmental design. This is about ensuring that your environment makes it as easy as possible to be focused.

Another valuable lesson is creating systems for the different parts of the business. With a newsletter, it’s important to have a system of curating articles/information that you can use in upcoming issues.

Lastly, It’s important to be courageous. This means launching even if you’re scared or feel that you’re not ready. You never know what you’re capable of building. You learn so much by doing and making mistakes along the way. These “mistakes” eventually set you up for success. Side project or otherwise, building something and filling a need

What platform/tools do you use for your business?

Namecheap, Carrd, Revue, Twitter, Quora, Upwork, Grammarly, Revue Chrome Extension, Pomodoro Timer, OneTab, Stripe, PayPal.

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

Atomic Habits by James Clear

The 4 Hour Workweek by Tim Ferris

  • I love how it simplifies the idea of remote entrepreneurship and location independence. It makes it very tangible and breaks down strategies for courageous entrepreneurs to follow.

The Black Box by Marquett Burton

  • Marquett Devon Burton is a refreshing figure because of his background. He went from living in abject poverty and being raised by an addicted mother to a successful tech entrepreneur by way of studying at UC Berkeley and Johns Hopkins. The storytelling in the book is amazing and there are a lot of gems dropped.

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

  1. Do it scared
  2. You’re capable of more than you think
  3. Learn to rest, but don’t give up when things get hard

Where can we go to learn more?

If you have any questions or comments, drop a comment below!