How I Built A $24K/Year Newsletter Side Hustle That Shares Remote Workspaces And Got Acquired

Published: October 1st, 2022
Ryan Gilbert
Founder, Workspaces
started May 2020
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Hello! Who are you and what business did you start?

Hi! I am Ryan Gilbert and I publish a weekly newsletter called Workspaces.

Workspaces was an idea born roughly two years ago when the pandemic had people shifting to a more remote environment. The goal of the newsletter was to give readers a behind-the-scenes tour of their favorite entrepreneurs, designers, developers, etc. new desk setups as they also shifted into this new workstyle.

The newsletter was recently acquired by YC startup Loops and I have joined the team as Head of Content to continue publishing Workspaces among other content and marketing initiatives. The newsletter was making $2,000 per month from sponsorships ($250 per slot / 8 editions per month) and is sold out for months at a time.

This was not an overnight success. It was quite the opposite. I published the first 117 editions before I made a single dollar from the project.


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

When I started Workspaces, I was working in supply chain management for a large (10,000+ person company). I had always wanted to move into tech but without coding knowledge, this always seemed like a pipedream.

I began seeing users that I looked up to on Twitter posting pictures of their new setups and it instantly occurred to me that these amazing spaces should be collected and preserved for longer than the Twitter algorithm would allow for. I instantly set up a Substack and sent a few texts and DMs to my first featured guests.

To simply learn how newsletters worked (Substack specifically since I couldn’t log in to Twitter without seeing someone promoting their new newsletter) and to hopefully gain a few new connections in the tech world, I published the first edition the next weekend and have not missed a scheduled publishing date since.

I actually had to increase the publishing cadence from 1x per week to 2x per week due to the growing backlog of people interested in sharing their workspaces with the community.

Today, there are 100+ workspaces in the backlog (I’m beginning to brainstorm ways to tackle this!) and I have to do very little cold outreach to get amazing guests. With the social proof of some of their peers and coworkers sharing their workspaces with me, new guests now come to me! :)

The success of the newsletter also helped pivot my career from supply chain to tech, first landing me a role at Product Hunt (a company I had always dreamed of someday working at).

Take us through the process of designing your MVP

Getting Workspaces up and running was the true definition of an MVP. I settled on Substack for ease of use - I didn’t even have my own domain at the time.

The entire process of getting the landing page up was ~5 minutes.

I would later buy once it was clear that this was becoming more than a side project. I’d say this was roughly around the 500 subscriber mark. Nothing crazy subscriber wise, but this was the point when I realized I could ask a generic question in the newsletter and would actually have readers respond to me! Crazy! Not only was I gaining subscribers but they were engaged enough to take the time to respond to my emails now too!

I run the entire newsletter out of Twitter DMs (for initial outreach), GMail (for sending the requirements, getting the content, etc), and Notion (for a simple sponsor calendar).

Today the newsletter is growing faster than ever. It has 9,000+ subscribers and sponsor slots are sold out months in advance.

The costs of running this newsletter are as close to $0 as you could possibly get. I spend about 2 hours on each edition (communication, formatting, sending, Twitter, etc). Altogether, I spend 4 hours per week on the newsletter, max.

Describe the process of launching the business.

Once I had the Substack landing page up I sent out a few texts and Twitter DMs. The first to answer and share their workspace was Shiv, who I knew from a previous side project. He quickly emailed me a picture of his desk and a list of items that helped him do his best work.

Once this first workspace was published it was very easy to confirm future guests as I had a solid example to show them.

It was important to me to keep the requirements of the guests as manageable as possible so that they wouldn’t become overwhelmed and back out midway through the process.

This simple process and website setup are what got me to $2,000 per month in revenue and nearly 200 published workspaces. Going from an idea to something that was “out there” in 5 minutes was important to make sure I stuck with it. Once I reached out to guests, there was no turning back.

It’s okay to gather feedback and iterate along the way but don’t let this slow you down and/or put a pause on your consistency.

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

Consistency. Consistency. Consistency.

Since starting Workspaces, I have not missed a scheduled publishing date (Saturday and Sunday). This consistency has allowed readers to confidently open their email with their weekend coffees and dive into new workspace inspiration.

Outside of simply being consistent, leaning on my guests’ social followings has been the biggest growth driver of the newsletter. This is something that I planned from the beginning and I’m glad it proved to work.

The guests are proud of their workspaces - which is why they are sharing them in the first place - which has also made them very likely to share my post about them after I publish it.

Being able to leverage guests like Joey Banks or Allan Grinshtein has proven to be a critical growth lever.

This has in turn grown my own audience and has led to a very engaged community.



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

Today the newsletter is growing faster than ever. It has 9,000+ subscribers and open rates are still hovering around 60%.

Substack had gotten me to this point but it was time to think bigger.

The acquisition by Loops couldn’t have come at a better time. They had recently sponsored an edition of the newsletter and saw an immediate positive ROI which opened the door for a “crazy idea”, in their words. We hopped on a call and quickly discovered that we shared a love for email and the power of a connected audience.

They understood that I wasn’t interested in simply selling the newsletter and parting ways with it completely. Afterall, this was the “side project” that allowed me to transition into tech in the first place.

I valued the opportunities and connections that it gave me more than the additional income stream. So we agreed that with the acquisition, I’d also go with Workspaces to join the Loops team as Head of Content and employee #1.

Once the acquisition was finalized, we quickly got to work on the new website. With that came a Product Hunt launch that earned Workspaces #1 Product of the Day and #4 Product of the week. I could not have wished for a better transition post-acquisition.

There will now be more giveaways and similar things to keep loyal readers engaged. More fun on Twitter/Instagram… channels that I have largely used to simply repost the weekly newsletter content to this point.

Overall, much of the same going forward but in a more useful and thoughtful way.

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

The main thing that I have learned is that consistency > is everything. I truly mean that. It took me 422 days to get the first 1,000 subscribers. It would have been very easy to give up after a slow start.

Consistency is the only thing that allowed Workspaces to grow to where it is today.

What platform/tools do you use for your business?

Currently…Webflow, Loops, Gmail, Twitter, Notion.

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

I have been loving My First Million from Sam Parrand Shaan Puri lately on the podcast side of things. The casual conversations while dropping nuggets of insightful information make it a weekly listen.

Other than that, Twitter has been invaluable for networking and learning as I go.

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

Just get started and don’t stop.

It’s okay to gather feedback and iterate along the way but don’t let this slow you down and/or put a pause on your consistency.

Where can we go to learn more?

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

Ryan Gilbert, Founder of Workspaces
Pat Walls,  Founder of Starter Story
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