I’ve been thinking a lot about domains lately.
Part of that comes from conversations with ChatGPT, where the topic of owning a lot of domains keeps surfacing. Not just domains, but courses, tools, themes, hosting, keyword research software. All the things you tend to accumulate when you spend years trying to build something online.
When you look at it all at once, it’s easy to feel conflicted. There’s time and money invested. Some projects became real. A lot of them didn’t. And when there isn’t a clear win to point to, it’s hard not to ask yourself whether you were just half-assing things or chasing ideas without ever finishing them.
I don’t think it’s failure exactly. But it’s not nothing either. It’s bittersweet.
Almost all of my domains were purchased through NameSilo. One or two through Namecheap. I’m not going to go through all thirty-plus of them. That would just turn into a list. What’s more interesting are the patterns.
The first domain I ever bought was CrucialWorkout.com. That came from taking James Lee’s Affiliate Site Empire course. At the time, I was really into kettlebells and workout equipment and figured I’d build an affiliate site around that. It was also the moment I realized I knew absolutely nothing about WordPress. That domain never really got off the ground, and not long after, my focus shifted.
That shift led straight into dropshipping.
HeatRejuvenate.com became the center of that phase. That wasn’t just an idea. It had suppliers, customers, infrastructure, phone calls, an LLC, inventory sheets, and actual sales. If there’s one domain that clearly had the highest ceiling had I stuck with it, it’s that one. No question.
Some domains stayed with me because of the name more than the project.
RebootTheMission.com is one of those. It’s based on a song by The Wallflowers. I liked the idea of second acts and starting over. Helping people who spent their lives doing one thing and wanted to try something new online. I’ve never quite figured out what it should be, but I’ve also never been able to let it go.
DeadwaxDiaries.com is another. Stories behind albums. Recording sessions. Band turmoil. Liner-note-style writing. If I didn’t have other projects competing for time, I’d probably still be working on that one.
Eventually, everything circled back to WaylonPiper.com. At one point I tried splitting things up. A freelance writing site. A mission site. A personal site. In the end, using my own name made more sense. These notes live here now, and that feels right.
Some domains were just fun.
LivingDeadGamer.com came from a Rob Zombie song title and the image of zombies playing video games. I always imagined it as a print-on-demand brand. The name stuck with me so much that I actually repurchased it after letting it expire. Crucial Workout expired again and stayed gone. Living Dead Gamer didn’t. That probably says something.
PromptJuice.xyz exists because I wanted to build something, not because I expected it to become a business. The .xyz made sense. It was cheap, low-pressure, and experimental. I still update the plugin. It’s mostly for me, and that’s fine.
Then there are the ones that sting a little.
PumpUpTheVolume.io is the one I regret letting go too early. I loved that name. Still do. I don’t even know what it should have been, which is probably why I let it expire, but I remember feeling a real twinge of regret when it did. I could buy it back. I just haven’t decided if it deserves another chapter.
At some point, buying domains stopped feeling exciting and started feeling heavy. I think that happened when renewal time came around for the .io and .co domains. Especially the .io. That extra renewal cost for something with nothing attached to it felt different. It wasn’t just ten bucks to keep an idea alive. It was real money going out for something that wasn’t moving.
Did buying domains ever feel like progress when I was actually stuck?
Maybe. I don’t think it was the domains themselves as much as the feeling of starting something new. A fresh slate. Another creative direction when the current one got uncomfortable.
Lately, I’ve been wondering if voice notes would have changed the outcome of some of these projects. I’m starting to think they might have. I’ve found a rhythm using them on this site that I never had before. If I’d talked through ideas instead of trying to write everything the “right” way, maybe some of those sites would have gotten further. Maybe not. But this feels more honest.
At this point, I’m down to about six or seven domains. By the end of 2026, it’ll probably be four or five. Fewer projects. More focus. At least that’s the idea.
I don’t regret buying the domains. I don’t regret most of the time spent on them either. Every one of them taught me something. Even the ones that went nowhere.
This is just me taking inventory.
