Running a $2k/month newsletter side hustle showcasing workspaces

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Hello there! Tell us about yourself and what is your business?

Hi! I am Ryan Gilbert and I publish a weekly newsletter called Workspaces.
Workspaces is a newsletter that feature the desk setups and workspaces of entrepreneurs, designers, developers etc.
The newsletter was recently acquired by YC startup Loops. I then joined the team as Head of Content to continue publishing Workspaces among other content and marketing initiatives.

Why and how did you start this business? Take us through the process

Back in 2020, when the pandemic had just started, people were shifting to a WFH environment. I decided to start a twice-weekly newsletter that gives readers a behind the scenes tour of their favorite entrepreneurs, designers, developers’ desk setups.
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).
I published the first 117 editions of the newsletter without a sponsor and without an idea on where I was going. I’m glad that I perserved as it all kind of worked out in the end.

How does the business make money?

The newsletter make $2,000 per month from sponsorships ($250 per slot / 8 editions per month).
I had roughly 3,300 subscribers when I started looking for sponsors. With the exception of one sponsor, all other sponsors have been inbound. To start I added a blurb in the intro of a newsletter stating that I was looking for sponsors and the numbers to date. I immediately received replies + DMs and was quickly booked out months in advance. The exception was Baronfig. I just thought they would be a great fit so I cold-emailed them and they immediately booked two slots while offering a discount to my readers.
Since then, the newsletter has been sold out weekly and the price has risen from the initial $150 to $250, earning $2,000 per month from sponsorships.

How did you get your initial subscribers / customers?

It took 716 days and 139 featured setups for Workspaces to hit 5,000 subscribers.
Here is a timeline:
0 to 1,000 → 422 days
1,000 to 2,000 → 77 days
2,000 to 3,000 → 107 days
3,000 to 4,000 → 62 days
4,000 to 5,000 → 48 days
I have featured 167 workspaces to date (70 more in the backlog) and have grown the newsletter to 6,500 subscribers while maintaining a >50% open rate.
I think it’s important to note that this was not an immediate cash cow… sending out 117 editions of a newsletter without receiving a dime can be draining. You have to truly enjoy the content you are putting out (I do!).

What are your marketing strategies in getting and retaining customers?

For growing my subscribers, I decide that producing content that is not only shareable in a social setting (in my case Twitter) but also able to loop in/tag other people and their communities.
Leaning on others as a growth lever probably seems like common sense but is often overlooked.
Every time I share a workspace, I was able to tag that person on Twitter and ask them to share it with their community which leads to an immediate bump in views and subscribers.
I posted all of the newsletters as a blog post on Twitter as well - tagging all of the featured guests. 99% of them retweeted it or created a tweet of their own to share their space!
Over time, this snowballed and people actually organically started mentioning me in tweets of others spaces to get me to include them in a future edition.
I started out looking for guests with large Twitter followings (I still do but less so now if the workspace itself is great). All but 5 or so have gone on to retweet or share their workspace post, which helps to spread the word around my newsletter.
Other than that, consistency rules and as long as you continue to show up, put out great content and iterate based on feedback you will continue to see your newsletter grow and ultimately the money will come.

What is one advice you would give to other founders who is starting out?

Consistency > everything. It took me 422 days to get the first 1,000 subscribers. I could have tons of reasons to give up after a slow start but I didn’t.
Consistency is that one thing that allowed Workspaces to grow to where it is today