Lessons from a Failed Newsletter: Why My Newsletter Didn’t Work—and What I Learned

Starting a newsletter feels exciting at first. You have a vision, a goal, and (hopefully) the drive to see it through. That’s exactly where I was when I launched Brands on the Block. For over a year, I wrote weekly updates tracking how brands used emerging tech to create new ways of engaging their audiences. Blockchain, NFTs, gaming, AI, AR/VR—you name it.

But after 65 posts, I realized it wasn’t working. The subscribers didn’t show up, and the excitement I once had for the project began to fade. Here’s what I learned from that experience—and how it’s shaping what I do next.

The Spark: Why I Started “Brands on the Block”

When I launched, my vision was clear: create a tracker for how brands use new tech in creative ways. I’d been working on innovative projects myself, but staying on top of what other brands were doing felt impossible. There wasn’t a resource that gave consistent, general updates, and I wanted to create something I wished I had—a simple, digestible newsletter (and shortly after a Notion database) for inspiration and trend-tracking.

At first, I felt energized by the challenge. I had some experience with blockchain and NFTs, which felt like the future of engagement at the time. The projects I was seeing were incredibly creative, and I wanted to showcase how brands were experimenting with these technologies. I bought a domain, set up tracking, and started collecting subscribers. It felt legitimate—like I was building something real.

What Went Wrong

1. Shifting Market Trends
   The content I originally planned to focus on—blockchain and NFTs—lost momentum. Within a few months, most of the activations shifted to gaming and platforms like Roblox. While I found AI projects exciting to cover, tracking Roblox integrations felt repetitive and uninspired. The creativity that drew me in initially wasn’t there anymore.

2. Too Niche of an Audience
   Just because I wanted this content didn’t mean others did. The audience for a newsletter like this was incredibly niche, and while there was chatter on platforms like LinkedIn, it didn’t translate to actual subscribers for me.

3. Rigid Format, Limited Flexibility
   I boxed myself into a structured, informational format. While it looked polished, it left no room for experimentation. It became a task to complete, rather than something I felt passionate about.

4. Saturated Medium, Overwhelmed Inbox
   Newsletters face tough competition in people’s inboxes, and mine didn’t break through. Without a strong social presence to back it up or a clear, compelling value proposition, it struggled to get noticed.

What I Learned

1. Flexibility Matters
   Being too rigid with format or cadence can kill creativity. For this newsletter, I’m taking a more flexible approach—sharing content when I feel inspired, in a more conversational and personal tone.

2. The Audience Comes First
   Content needs to deliver value. With Brands on the Block, I focused on what I wanted to create rather than what others needed. Moving forward, I’m thinking more intentionally about what’s actually useful or engaging for others—moments of awe, inspiration spikes, or information I feel worth sharing.

3. Social Presence Is Key
   Building a newsletter without an established personal or social presence is an uphill battle. Engagement doesn’t just happen—you need to invest in creating conversations, commenting, and building trust with your audience.

4. The Power of Automation
   As Brands on the Block grew, so did the workload. To save time, I experimented with automation tools like Make.com linked to Google Sheets and AI platforms like Claude, Perplexity and ChatGPT. The goal was to streamline tasks like gathering data, drafting summaries, formatting posts, and social content creation. While the results weren’t always perfect, the process taught me valuable lessons about optimizing workflows and leveraging AI tools. These skills will be invaluable as I explore saving time on new ventures.

5. Not Every Idea Will Work—and That’s Okay
   This experience showed me the importance of trying things, even if they don’t pan out. It’s a stepping stone, not a failure. The time spent experimenting has helped me refine my focus and develop new skills.

Knowing When to Move On

One of the hardest lessons was learning when to stop. After over a year of weekly posts, it felt wrong to let go of something I’d worked so hard on. But I came across a quote that stuck with me:

The newsletter wasn’t helping me climb the right mountain anymore. The lack of growth and my own waning interest were clear signals it was time to pivot. As tough as it was to stop, the first week without the newsletter felt like a weight lifted. I knew I’d made the right decision.

Advice for Anyone Starting a Newsletter

1. Test Your Idea First: Don’t assume people want what you want. Try different formats, topics, and platforms to see what resonates.

2. Build Your Presence: Social engagement matters. Comment, post, and build relationships to draw attention to your content.

3. Prioritize Value: What’s in it for the reader? If your content doesn’t feel like a “must-open,” it’s unlikely to stand out.

4. Be Flexible: Give yourself room to experiment. If something doesn’t work, pivot. Don’t let structure stifle creativity.

5. Don’t Be Afraid to Move On: Sometimes, persistence isn’t the answer. Recognize when something isn’t working and redirect your energy to something that excites you.

What’s Next

While Brands on the Block didn’t achieve what I hoped, it taught me so much about showing up, being consistent, and learning from the process. With Chasing Next, I’m focusing on what excites me—new ideas, personal growth, and sharing tools and lessons. Who knows where it’ll go, but I’m energized by the possibilities.

DISCLAIMER: This content does not contain business, investment, tax, legal, financial or other advice & is not intended to be used in this way. It includes the opinions of the author & is strictly for informational purposes. Please do your own research.