How Ryan Gilbert Turned Workspaces Into a $250-Per-Slot Revenue Machine in the Remote Work Industry

Founder: Ryan Gilbert
Business: Workspaces
Revenue/Month: $2K
Founders: 1
Employees: 0
Website: workspaces.xyz
Location: Remote
Founded: April, 2020

Workspaces began as a simple idea in a world turned upside down. Two years ago, amid the uncertainty of a pandemic that blurred the lines between home and office, Ryan Gilbert created a newsletter that would soon capture the imaginations of thousands. What started as a modest weekly email, exploring how people adapted their desks and workflows to fit the new reality of remote work, has since grown into a thriving platform under the wing of YC startup Loops. 

“At the time, everyone was trying to figure out this new way of working,” says Gilbert. “There was this collective curiosity about how others were making it work—how they were setting up their desks, what tools they were using, how they were finding focus.” 

Workspaces struck a chord. The newsletter offers more than just visual inspiration; it gives readers a glimpse into the lives and workstyles of entrepreneurs, developers, and designers. From standing desks adorned with meticulously arranged tech to sunlit nooks brimming with books, plants, and personality, each feature tells a story about the individual behind the setup. 

“It’s not just about the aesthetics,” Gilbert explains. “The workspace is such a personal thing. It reflects your habits, your goals, even your quirks. I wanted to capture that—how people mold their environments to make their work, and their lives, better.” 

But turning an idea into something sustainable didn’t happen overnight. Gilbert recalls the early grind vividly. For two years, he published every week—117 issues in total—without earning a cent. “Honestly, there were times when I wondered if it was worth it,” he admits. “But I just kept going. I believed in it.” 

Eventually, that belief paid off. When sponsorship opportunities began to materialize, they came with momentum. Companies lined up to pay $250 for a coveted spot in the newsletter, and every slot was sold out months in advance. With eight editions a month and a consistently engaged audience, Workspaces became not only a creative outlet but also a sustainable business. 

“People sometimes forget how much work goes into something like this,” Gilbert says. “It’s not just about writing and publishing. There’s research, building relationships with sponsors, growing the audience. But once it started to click, it really clicked.” 

One of the keys to Workspaces’ appeal is its universality. No matter what someone does for a living, their workspace is often deeply personal. “Everyone has a desk,” Gilbert notes with a laugh. “It doesn’t matter if you’re a CEO or a student—your workspace is where a lot of your life happens.” 

Gilbert has a knack for identifying the details that make each setup unique. A recent edition highlighted a creative director’s desk outfitted with retro-inspired design touches, complete with a Polaroid camera and vintage record player. Another showcased a software engineer’s minimalist standing desk, optimized for efficiency with a single monitor, mechanical keyboard, and ergonomic chair. 

“I love when people tell me they’ve been inspired to rethink their own spaces,” Gilbert says. “Sometimes it’s as small as adding a plant or a new lamp, but those little changes can make a big difference.” 

The newsletter’s success is also a testament to its ability to reflect a broader cultural shift. As hybrid work becomes the norm and people continue to reimagine how they balance professional and personal life, Workspaces has become a kind of digital gallery—a place where readers can see themselves and their ambitions reflected. 

“At the end of the day, it’s about more than desks,” Gilbert says. “It’s about how we work, why we work, and how we’re creating environments that support us, not just as professionals but as people.” 

From Supply Chains to Substack: A Vision Finds Its Voice 

Before Workspaces became a hub of creativity and insight, Gilbert was miles away—both figuratively and literally—from the tech world he longed to join. His days were spent in supply chain management at a massive organization with over 10,000 employees, a far cry from the agile and innovation-driven environment of startups. Yet, as he tells it, the limitations of his day job sparked a hunger for something more. 

“I didn’t know how to code. I didn’t have a traditional path into tech,” Gilbert recalls. “It felt like this huge wall I couldn’t climb. But sometimes, when you’re stuck, you start paying closer attention to the things around you.” 

For Gilbert, inspiration arrived in an unlikely package: a casual scroll through Twitter. As he browsed, he began noticing a trend—people sharing snapshots of their home office setups. There was something captivating about these posts, from meticulously organized workstations to cozy corners filled with personal touches. They offered fleeting insights into how others were not only surviving the upheaval of the pandemic but also redefining the way they worked. 

“It was this little slice of their lives, a mix of personality and practicality,” he says. “I started to think, ‘What if there was a way to collect these stories and give them more permanence?’ That’s when the idea for Workspaces clicked.” 

Armed with nothing more than an idea and Substack as his chosen platform, Gilbert moved quickly. He reached out to a handful of people in his network, asking if they’d be willing to share their setups for what would become the inaugural issue. “I wasn’t even sure anyone would respond,” Gilbert admits. “But I figured, why not try?” 

The first edition went live just days later, a short and focused email that showcased a few curated setups. From the start, Gilbert committed to consistency, vowing to publish weekly no matter what. “The key was showing up,” he says. “Even when the subscriber count was low, even when I wasn’t sure where the next feature would come from—I just kept hitting publish.” 

Building Momentum, One Feature at a Time 

As the newsletter gained traction, it quickly became clear that there was a growing appetite for the kind of content Gilbert was creating. What had started as a once-a-week passion project soon required twice-weekly editions to keep up with demand. Submissions began pouring in from readers eager to showcase their own workspaces, and before long, the challenge shifted from finding contributors to managing a queue that now exceeds 100 profiles. 

But the early days required grit and persistence. “It wasn’t like people were lining up to be featured,” Gilbert says of the beginning. “I spent a lot of time sending cold messages, asking people to give this unknown newsletter a chance.” Slowly but surely, word began to spread. Featured guests shared their profiles with their own networks, creating a ripple effect that expanded Workspaces’ audience far beyond Gilbert’s initial reach. 

The snowball effect wasn’t limited to the newsletter’s growth—it also had a profound impact on Gilbert’s career. As Workspaces gained visibility, so did Gilbert, opening doors he once thought closed. The project served as both a portfolio and a proof of concept, showcasing his ability to build an engaged community from scratch. 

“I started Workspaces because I wanted to be part of the tech world,” Gilbert reflects. “What I didn’t expect was that it would be my way in.” 

Eventually, his work with Workspaces caught the attention of Product Hunt, a company Gilbert had long admired. Joining their team marked a pivotal moment—a shift from the constraints of supply chain management to the creativity and energy of the tech industry. “I was finally where I wanted to be,” he says. “And it all started with this tiny idea I couldn’t let go of.” 

Building Workspaces: Growth Through Focus and Opportunity 

From its inception, Workspaces has been a masterclass in simplicity and efficiency. Gilbert was deliberate about starting lean, launching the newsletter without overcomplicating the process. There was no custom website, no elaborate branding—just a Substack landing page created in under five minutes. This streamlined setup let him zero in on what really mattered: finding engaging workspace stories and delivering them to readers. 

“I didn’t want to get bogged down in the tools,” Gilbert says. “The faster I could get the first issue out, the sooner I could focus on building something people actually cared about.” 

That same clarity extended to his guest outreach strategy. Early on, Gilbert relied on Twitter and text messages to pitch his idea to potential contributors. He kept the process simple, minimizing effort for his guests. “I wanted to make it easy,” he explains. “The ask was clear: send a photo, answer a few questions, and you’re done. No extra back-and-forth, no heavy lifting.” 

This low-friction approach not only encouraged participation but also set a tone of accessibility that has become a hallmark of Workspaces. Guests, many of whom are professionals with demanding schedules, found the process so painless that they were eager to share their features with their networks. It was a smart play by Gilbert—every share brought a surge of new readers, helping the newsletter grow exponentially. 

Scaling Through Simplicity 

Even as the newsletter grew, Gilbert’s operation remained impressively lightweight. Each issue required about two hours of work, split between guest communication, formatting, and social media promotion. With just four hours a week dedicated to the project, Gilbert maintained a steady rhythm of two issues per week, a pace that became a cornerstone of Workspaces’ success. 

“People underestimate the power of consistency,” he says. “It’s not about working around the clock; it’s about showing up on schedule, every time.” 

Consistency not only solidified his audience’s trust but also helped attract advertisers. Sponsorship slots, priced at $250 each, quickly sold out months in advance, providing reliable revenue with minimal overhead. 

Gilbert also tapped into a brilliant organic growth strategy: the pride people take in their workspaces. “Everyone loves showing off their setup,” he explains. “When someone’s feature goes live, they share it with their followers. That’s how we’ve been able to grow so much—through the networks of the people we feature.” 

By including high-profile contributors like Joey Banks and Allan Grinshtein, Gilbert amplified this effect, extending Workspaces’ reach far beyond its original audience. With over 9,000 subscribers and open rates consistently hovering at an impressive 60%, the newsletter cultivated not just a readership but a community of engaged professionals who returned week after week. 

Joining Loops and Expanding the Vision 

As Workspaces gained momentum, Gilbert began to see its potential for something bigger. While Substack had been instrumental in launching and scaling the newsletter, its limitations became apparent as the project grew. The need for additional resources and broader capabilities paved the way for a pivotal acquisition by Loops, a YC-backed startup that had initially supported Workspaces as a sponsor. 

For Gilbert, the decision to sell wasn’t purely about the financial upside. “Workspaces wasn’t just a newsletter to me,” he says. “It opened doors I never thought I’d walk through. It connected me to incredible people and gave me a way into the tech world. I didn’t want to let that go.” 

The acquisition came with a new role—Head of Content at Loops, making Gilbert the company’s first hire. This move was as much about growth as it was about preserving the heart of Workspaces. Under Loops, Gilbert has been able to expand on the project’s success, introducing new initiatives like giveaways, collaborations, and a stronger social media presence to further build the community around the newsletter. 

The redesigned Workspaces website, launched through a high-profile Product Hunt campaign, brought the project even more visibility. Garnering the #1 Product of the Day and #4 Product of the Week, the launch was a validation of Workspaces’ enduring appeal. 

But despite these changes, the core of Workspaces remains the same. “The mission hasn’t changed,” Gilbert says. “It’s still about showcasing people’s workspaces and telling their stories. We’re just finding new ways to make it better.” 

The Slow Build: How Consistency Drives Results 

When Gilbert launched Workspaces, he knew success wouldn’t happen overnight. The newsletter’s early growth was painstakingly slow—422 days passed before it hit 1,000 subscribers. In an era where viral success stories dominate the narrative, such a gradual climb might have been enough to dishearten most creators. But for Gilbert, the slow pace only reinforced the importance of persistence. 

“I remember refreshing the subscriber count and thinking, ‘Is this really going anywhere?’” he says. “But the thing is, I didn’t start this to blow up overnight. I started it because I thought the idea mattered. So I kept going.” 

Each week, a new issue landed in readers’ inboxes, regardless of how many people were on the list. This unwavering rhythm became the lifeblood of Workspaces. By showing up consistently, Gilbert created a sense of dependability that resonated with readers. Over time, the trust he built began to compound. “When people see that you’re consistent, they start to trust you more,” he explains. “That trust is what keeps them coming back.” 

Turning Consistency Into Momentum 

The slow start wasn’t just a test of patience—it was a lesson in how incremental progress can snowball over time. Every issue Gilbert published became part of a growing library of content, adding substance to the newsletter and making it more appealing to new readers. “The archive itself became a selling point,” he says. “When someone signed up, they didn’t just get the latest issue. They got access to everything that came before it.” 

This approach also helped attract sponsors. The longer Gilbert stuck to his publishing schedule, the more legitimacy Workspaces gained as a platform. Advertisers began to see it not as a flash-in-the-pan project, but as a reliable outlet with a steady audience. 

“Sticking to a schedule wasn’t just about discipline,” Gilbert says. “It was about creating a foundation that people could trust. Whether you were a reader or a sponsor, you knew what to expect.” 

Beyond the metrics, the act of showing up consistently sent a message. It demonstrated that Workspaces wasn’t a passing experiment or a half-hearted side gig. It was something built to last, something Gilbert believed in enough to invest his time and energy week after week. 

“People underestimate the value of simply being consistent,” he adds. “It’s not the most glamorous part of building something, but it’s the part that keeps everything else moving.” 

By the time Workspaces reached its first 1,000 subscribers, the momentum was undeniable. What started as a trickle became a steady flow, with each milestone paving the way for the next. The lesson, as Gilbert puts it, is simple: “If you keep showing up, eventually people start paying attention.” 

Starting Fast, Growing Steady: Lessons for Entrepreneurs 

For many entrepreneurs, the biggest obstacle is often the one that comes before anything else—the fear of starting. Questions of whether an idea is “good enough” or if the timing is right can lead to endless delays. Gilbert, however, tackled that challenge head-on with Workspaces, proving that momentum often matters more than perfection. 

“I could’ve spent weeks overthinking every little detail—what the branding should look like, what tools I should use, whether or not I was ready,” he recalls. “But at some point, you just have to get out of your own way and start.” 

Progress Over Perfection 

Gilbert’s decision to launch Workspaces quickly, using a simple Substack page, allowed him to avoid the analysis paralysis that stymies so many first-time creators. By cutting through the noise of unnecessary decisions, he focused entirely on his core vision: showcasing how people personalize their work environments for creativity and productivity. That clarity in purpose made it easier to take action—and taking action, he believes, is where everything begins. 

“Starting with something basic doesn’t mean you’re cutting corners,” Gilbert says. “It means you’re giving yourself room to figure things out as you go. You can’t refine something that doesn’t exist.” 

From there, it was about consistency. Week after week, he showed up—sometimes for an audience of only a few hundred, sometimes questioning whether it was all worth it. But publishing regularly gave him the chance to improve and allowed readers to connect with the project. Over time, the small steps added up. 

“The only way you build trust is by showing people you’re serious,” Gilbert says. “It’s not about having the perfect product from day one. It’s about proving that you’ll stick with it, that you’re not going to disappear after a couple of weeks.” 

Momentum is Everything 

Gilbert believes the key to building something meaningful is momentum. Once the idea is out there, it becomes easier to iterate, expand, and refine. For Workspaces, what began as a simple concept has grown into a full-fledged platform—complete with a loyal subscriber base, sold-out sponsorship slots, and a broader reach thanks to the acquisition by Loops. 

But none of that would have happened if Gilbert had waited for the stars to align. “You don’t need perfect conditions to start,” he emphasizes. “You just need to start. Everything else will fall into place as long as you keep going.” 

For aspiring entrepreneurs, Gilbert’s journey offers a roadmap rooted in simplicity and persistence: Take the first step, focus on what truly matters, and never underestimate the power of showing up. Workspaces is proof that a strong idea, paired with consistent execution, can grow into something far bigger than its creator ever imagined. 

Success Factors: Why Did Workspaces Succeed? 

  • Simplicity and Starting Lean: Gilbert launched Workspaces with minimal resources, using accessible tools like Substack to quickly get started. Instead of overcomplicating the early stages with unnecessary details like custom websites or elaborate branding, he focused on getting the newsletter live and letting the idea speak for itself. “I didn’t want to get bogged down in the tools,” he explained, which allowed him to move past the mental hurdles that stop many entrepreneurs from starting. 
  • Consistency and Reliability: Gilbert’s commitment to publishing new issues on a regular schedule—without missing a single date since the first issue—built trust with his audience. Readers came to depend on the newsletter as part of their routine, and this reliability fostered a sense of loyalty. “When people see that you’re consistent, they start to trust you more,” he said. This consistency also made the newsletter appealing to sponsors. 
  • Focus on the Core Idea: From the beginning, Gilbert kept his focus sharp: Workspaces was about showcasing unique and inspiring desk setups that reflected people’s workflows and personalities. By staying true to this clear and relatable concept, he created content that resonated deeply with his audience. “The workspace is such a personal thing,” he noted. This universality gave Workspaces broad appeal. 
  • Guest-Friendly Simplicity: Gilbert made it easy for contributors to participate. With minimal effort required—just submitting a photo and answering a few questions—featured guests were happy to share their setups. This low-friction process encouraged participation and helped fuel the newsletter’s growth. “The ask was clear: send a photo, answer a few questions, and you’re done,” Gilbert explained. 
  • Organic Growth Through Guest Networks: By featuring creators and professionals who were proud of their workspaces, Gilbert tapped into their networks when they shared their features with their followers. This strategy created a ripple effect, exponentially growing the newsletter’s audience with each new issue. Featuring prominent creators like Joey Banks and Allan Grinshtein amplified this effect, attracting larger and more engaged audiences. 
  • Patience and Persistence: Growth didn’t happen overnight. It took over a year to reach the first 1,000 subscribers, but Gilbert’s refusal to give up—despite the slow early progress—was critical. He understood that building something meaningful takes time and stuck with it, even when results were modest at first. “If you keep showing up, eventually people start paying attention,” he said. 
  • Monetization Through Sponsorships: Once Workspaces had an engaged and loyal subscriber base, Gilbert monetized effectively by selling sponsorship slots. These slots consistently sold out months in advance, providing a steady revenue stream without the need for significant overhead or expenses. 
  • Leveraging an Acquisition for Growth: The acquisition by Loops, a YC-backed startup, provided additional resources, allowing Workspaces to grow beyond its initial scope. Under Loops, Gilbert was able to refine the newsletter further, add features, and expand its reach—all while maintaining the core mission of the project. 
  • Staying Connected to the Audience: Gilbert understood his audience and what they cared about, keeping Workspaces personal, relatable, and engaging. By focusing on real-world stories, he created a community around the newsletter, reflected in impressive metrics like high open rates and loyal readership. 
  • Belief in the Idea: Above all, Gilbert’s belief in the concept of Workspaces kept him moving forward, even when challenges arose. His ability to focus on progress over perfection—”You don’t need perfect conditions to start”—was a key driver of success. 

Key Success Factors 

  1. Start Before You’re Ready: The hardest step in any project is often taking the first one. Gilbert didn’t wait for perfect conditions or a flawless plan; he launched Workspaces quickly using simple tools like Substack. This allowed him to focus on execution rather than getting bogged down in unnecessary details. Lesson: Perfection isn’t required to start. Taking action creates momentum and helps overcome the fear of imperfection. 
  1. Focus on Your Core Idea: Gilbert kept Workspaces simple and focused on one relatable concept: showcasing how people personalize their workspaces. This clear, narrow focus allowed him to connect with his audience deeply, rather than diluting the newsletter with unrelated content. Lesson: A clear and specific idea that solves a real need is far more effective than trying to do everything at once. Start small, and build on that foundation. 
  1. Consistency Builds Trust: Gilbert’s commitment to publishing regularly—without ever missing a scheduled date—became one of the newsletter’s defining characteristics. This consistency not only earned readers’ trust but also set the tone for sponsors and contributors. Lesson: Showing up consistently is critical. Trust and reliability are earned over time, and they form the foundation of long-term success. 
  1. Progress Matters More Than Perfection: The early versions of Workspaces weren’t fancy or polished. Instead of waiting to perfect every aspect, Gilbert launched quickly and improved the newsletter iteratively over time based on real-world feedback. Lesson: Don’t let perfectionism hold you back. Start small, learn from experience, and refine as you go. 
  1. Leverage Organic Growth: By featuring guests who were proud of their workspaces, Gilbert tapped into their networks. Guests shared their profiles with their own followers, creating a snowball effect that brought in new readers with every issue. Lesson: Find ways to involve your audience and contributors so that they become advocates for your project. Organic word-of-mouth growth can be far more effective than paid marketing. 
  1. Make It Easy for People to Participate: Gilbert designed a low-friction process for contributors, asking for just a photo and a few answers to simple questions. This made it easy for busy professionals to say yes, which helped him secure high-profile features early on. Lesson: Reduce the barriers for collaboration. The easier you make it for people to participate, the more likely they are to engage. 
  1. Patience Is Essential: Workspaces grew slowly at first, taking over a year to reach 1,000 subscribers. Many creators might have abandoned the project during this period, but Gilbert’s persistence paid off as small, steady wins eventually compounded into major growth. Lesson: Building something meaningful takes time. Be prepared to put in consistent effort, even when results are slow at first. 
  1. Consistency Creates Legitimacy: Publishing regularly not only built trust with readers but also gave the newsletter credibility with sponsors. Over time, Gilbert’s consistency proved that Workspaces wasn’t a fleeting side project but a reliable platform worth supporting. Lesson: Delivering consistently over time can position you as trustworthy and legitimate, even in crowded or competitive spaces. 
  1. Monetization Follows Value: Gilbert focused on creating a valuable experience for readers first, which made monetization easier when the time came. Sponsors quickly recognized the value of Workspaces’ highly engaged audience, allowing him to sell out advertising slots months in advance. Lesson: Focus on delivering value to your audience before thinking about monetization. When you’ve built something people care about, revenue opportunities will naturally follow. 
  1. Adapt and Expand When the Time Is Right: While Substack was the perfect platform to start, Gilbert recognized the need to evolve as Workspaces grew. The acquisition by Loops gave him access to more resources, enabling him to take the newsletter to the next level while staying true to its core mission. Lesson: Start with the tools and structure that make sense for where you are now, but be open to scaling and evolving as opportunities arise. 
  1. Momentum Drives Success: Gilbert’s ability to stay consistent and move forward, even during slow growth, created a sense of momentum that carried Workspaces to new heights. Every small step contributed to the bigger picture. Lesson: Small, consistent actions compound over time. Don’t underestimate the power of steady progress. 
  1. Believe in Your Idea: Above all, Gilbert’s belief in the concept of Workspaces kept him going through slow growth, self-doubt, and early uncertainty. That conviction drove him to persist, adapt, and ultimately build something lasting. Lesson: Passion and belief in your idea are the fuel you need to push through challenges and keep building, even when the results aren’t immediate. 

Opportunity Matrix 

Founder Background 

Ryan Gilbert had a background in supply chain management, working for a large company with over 10,000 employees. He aspired to enter the tech industry despite lacking coding expertise. 

Problem Identification 

During the pandemic, the shift to remote work led people to rethink their workspaces. Gilbert noticed a growing interest in workspace photos shared on Twitter, signaling an unmet need for inspiration and connection. 

Market Opportunity 

A growing audience of remote workers, entrepreneurs, and professionals were seeking inspiration, tools, and stories about creating personalized, functional workspaces. This market was underserved with focused content. 

Competitive Landscape 

While there are productivity blogs, YouTube creators, and general lifestyle content on workspaces, few platforms offered consistent, curated, and high-quality content about personalized desk setups. Workspaces occupied this niche. 

Market Research 

Gilbert observed trends on Twitter and identified organic interest in workspace photos. He tested his concept by reaching out directly to potential contributors and gauging interest through Substack subscriptions. 

Business Model 

Revenue was generated through sponsorships. Sponsors paid $250 per slot, and slots were consistently sold out months in advance due to the newsletter’s engaged and niche audience. 

Initial Capital 

Workspaces was bootstrapped with no significant initial investment. Gilbert relied on free or low-cost tools like Substack, Twitter, and minimal overhead costs to get started. 

Product/Service Development 

The newsletter began as a weekly publication featuring photos and stories about unique desk setups. Over time, Gilbert increased the frequency to twice a week and refined the process to feature high-quality content consistently. 

Marketing Strategy 

Organic growth through guest contributors sharing their profiles with their networks. Twitter was a key platform for Gilbert to engage with potential readers and contributors. Word-of-mouth played a significant role in expanding the subscriber base. 

Milestones 

  • First 1,000 subscribers in 422 days. 
  • Grew to over 9,000 subscribers with a 60% open rate. 
  • Achieved consistent revenue through sold-out sponsorship slots. 
  • Acquired by Loops (YC-backed startup). 
  • Product Hunt launch earned #1 Product of the Day and #4 Product of the Week. 

Scalability 

  • Workspaces can scale through: 
  • Expanding content formats (e.g., video, social media, and giveaways). 
  • Collaborations with brands targeting remote workers. 
  • Leveraging Loops’ resources to grow subscriber reach and refine the reader experience. 

Potential Risks and Challenges 

  • Reliance on niche content; risk of losing audience interest if the topic feels repetitive. 
  • Competition from larger platforms or creators who could replicate the concept. 
  • Balancing growth with maintaining the intimate, high-quality feel of the newsletter. 

Key Performance Indicators/Metrics 

  • Subscriber growth (9,000+ subscribers to date). 
  • Email open rates (around 60%). 
  • Revenue from sponsorships (consistently sold out months in advance). 
  • Engagement metrics on social media (shares, retweets, likes).