How Ryan Gilbert Leveraged His Side Project Newsletter into a Tech Dream Job

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

During the pandemic in 2020, Ryan Gilbert capitalized on the trend of remote workers sharing photos of their home workspaces by launching a side project newsletter called Workspaces. Within just two years, he grew it to over 6,000 subscribers and $2,000 in monthly revenue before exiting via acquisition - landing his dream job in tech.

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

Ryan was previously stuck in a dead-end supply chain job before he had the idea for Workspaces. He noticed workspace photos gaining traction on Twitter and quickly set up a Substack, sending out the first issue in April 2020. He was determined to build on this momentum, and hasn't missed a weekend publishing an issue since.

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

To create Workspaces, Ryan kept the format simple - featuring eye-catching photos and minimal text for easy weekend reading. For the first 50 issues, he cold DM'd people on Twitter asking to showcase their workspace. Once he had some samples to demonstrate the concept, booking guests became easier.

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

Today, Workspaces has over 32,000 Twitter followers and a months-long waitlist for creators wanting to be featured. Ryan has grown the newsletter to two issues per week, with $250 sponsorship slots providing $2,000 in monthly revenue.

In August 2022, the newsletter gained the attention of startup Loops, who acquired Workspaces and brought Ryan on as their first employee and Head of Content. He now gets to focus on creating full-time while still running Workspaces.

What platform/tools do you use for your business?

Ryan utilized Twitter as his main platform for growth, leveraging viral visual content. He also used Substack initially to publish issues easily. Other key tools he relied on were Gmail, Figma, Stripe, Webflow, Slack, Dropbox, and Twitter Polls.

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

Some of the most helpful resources for Ryan were the books "Traction" and "Explosive Growth." He also recommends the podcast How I Built This and newsletter Dense Discovery. Reading case studies of successful startups provided valuable insights.

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

Ryan suggests starting simple - don't overload yourself with too many tools right away. Find repeatable ways to get your content shared by leveraging guests/influencers in your niche. Be consistent in publishing on a regular schedule. Grow your audience before monetizing.

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Where can we go to learn more?

To learn more about Ryan's journey or explore issues of Workspaces, check out these links:

  • Ryan's Twitter
  • Workspaces Twitter
  • Ryan's interview on Indie Hackers
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