The Workspaces Journey

I’ve always wanted to work in tech. But what did this actually mean? I had no idea. It just sounded cool. And I heard there was $$$ to be made.

But after graduating school with a marketing degree in Wisconsin I couldn’t land a single interview at a SF startup. I didn’t have any experience, skills, or connections.

I wouldn’t have interviewed me either. Let alone actually hire me.

I ended up working in supply chain for 6 years. I spent a lot of my time watching the tech world from the sidelines through Twitter and TechCrunch.

But in April 2020 that would finally begin to change.

Workspaces is Born (April 2020)

It’s March/April 2020 and I begin to see a unique trend emerging on tech Twitter.

The COVID-19 pandemic is forcing more and more people out of the office and into a WFH environment.

More and more workers from the same tech companies I had previously applied to began posting pictures of their new setups… some from their couch or kitchen counter… some that looked to be $xx,xxxx setups that were carefully planned out.

I immediately knew that there was something here.

I quickly setup a Substack and texted the only loose connection to this world that I knew.

Workspaces was born.

I’d publish this very first edition on April 5, 2020.

Thankfully my social media game has improved a tiny bit since then.

(You can actually include the super shareable and beautiful desk pics IN the tweet 🤯)

Scrappy start.

We were officially off to the races.

Building Momentum

I had two strong beliefs when starting Workspaces.

1. Consistency would be key. I could not miss a single weekend once starting.

2. I could grow this entire thing off of the guest’s audiences. It did not matter that I did not have a following of my own.

My hunch was that if I could convince someone to share pictures of their setup with me that they would then also share the post after it was live, RT me, etc. Why else would they have taken the time to organize their space?

The consistency would allow this to snowball into a bit of a movement, with more and more people peeling back the curtains on how they were working in this new environment.

Both of these beliefs turned out to be true.

Every weekend I would share a beautiful WFH setup from someone working at a top tech company.

Every weekend that guest would share the post for me.

Every weekend my subscriber count and Twitter following would grow.

Rinse and repeat.

This flywheel led to something interesting happening after a few months. Instead of me sending 50+ cold DMs per week asking people to share their setup, people began reaching out to me asking to be included.

I now had a surplus of setups to share.

Monetizing Other’s Work

I had always had an aversion to monetizing Workspaces. I thought it would be weird to make money off of what was essentially the featured guest’s work — it was their setup and their words after all.

And my original goal with the project was simply to get something out there. Slowly build the connections in tech that I had desperately needed.

It would be more than 1.5 years of publishing every single weekend before I’d even consider it.

1.5 years of secretly publishing this newsletter. No one in my “real life” knew this existed. Story for another post.

But now I had started receiving inbound requests to sponsor.

I sent a note out to previous guests asking for their thoughts and explaining that I never planned on making money from this.

Surprisingly, all of them said to go for it.

On January 2, 2022 (edition 117) I let the 3,500 subscribers now that I would now be looking for sponsors.

I began charging $150 per ad slot.

due to demand quickly upped it to $250 per slot.

The newsletter was now making $1,000 - $2,000 per month with ads sold out weeks in advance. The range came from doing bundle deals with those who wanted to book more than one slot at a time.

“I had no idea it was that easy” 🙃

Fun times.

Acquired

On April 24, 2022 a startup fresh out of YC sponsored Workspaces.

Three days later I would receive this email.

On May 22, 2022 I accepted an acquisition offer that would make Workspaces a Loops publication and bring me on as their first employee and Head of Content.

Newsletter-wise, not much would change. I remained the “face” of the newsletter. We continued publishing every single week.

What was unique (and also made my life easier) was that we dropped sponsorships and instead opted to simply have it as a free publication from Loops, with minimal branding.

This move helped turn Workspaces from side project into something bigger.

We quickly moved off of Substack and onto a custom site.

For the next two years I would continue to publish Workspaces while at Loops.

During this time, my passion for the project would come and go, as it often felt like checking a box as part of a job.

I think this is normal as weeks without growth felt like it was my fault and weeks with crazy growth felt like I was missing out on all of the upside.

During this time… consistency was still priority #1. We had still never missed a single week of publishing (and was even publishing 2x per week for the majority of this time).

Re-acquiring Workspaces

After two years as Head of Content at Loops, I was laid off (May 2024).

However, it wasn’t all bad. In an unprecedented move that I’ll forever be thankful for, Loops allowed me to re-acquire Workspaces for $1.

$29 if you count the $28 wire fee.

A few $hundred if you count my car breaking down in the bank parking lot and needing to be towed.

Such is life.

I don’t know exactly why they offered the project back to me instead of keeping it or selling it to someone who would’ve surely paid more than $1 but it’s a move that I hope others do see and appreciate from their end.

This re-acquisition ultimately led to the very first weekend without a new workspace being published while details were ironed out.

I went for a hike with my wife and honestly… it was refreshing to not be thinking about Twitter and newsletters for the first time in years.

Future Outlook

Getting Workspaces back has been amazing. I have a renewed love and passion for the project.

The first order of business was getting the sponsorship flywheel going again. It’s a much different landscape than it was 2.5 years ago (much harder).

It’s starting to work but it’s definitely a month-to-month grind.

I’ve turned down 2 acquisition offers since re-acquiring it myself.

My love for newsletters has turned into a FT role at beehiiv.

Safe to say this little newsletter has changed my life.

P.S. I’ve done a handful of other interviews about Workspaces throughout the years. Some of this info can also be seen there in more detail. Some of the info here is fresh.

You can find the rest here:

Creator Spotlight

Hacker News

Indie Bites

Indie Hackers

Newsletter Circle

Next week I’ll be sharing my recent thoughts on experimenting with new monetization options for Workspaces and how a single tweet led to $1,000 hitting my bank account in 11 minutes.

Stick around.

-Ryan