The Domain Mistakes Startups Keep Making (And How to Not Be Dumb About It)

I've watched a lot of founders screw up their domain choices over the years. Not in obvious ways—nobody's out here buying DomainNameForMyStartup2025.biz—but in subtle ways that come back to bite them later. Sometimes way later, when fixing it costs ten times what doing it right would've cost upfront.

The frustrating part? Most of these mistakes are completely avoidable. But startups rush the naming process, or they overthink the wrong things, or they just don't realize what they're setting themselves up for. So here's what I keep seeing, and what you should probably do instead.

The "short at any cost" trap

Everyone wants a short domain. I get it. Three letters, four letters, something punchy and tight. Short domains can be incredible. But I've watched startups drop serious money on short domains that made absolutely no sense for their business, just because short felt premium.

You know what's not premium? Explaining your three-letter domain to every single person you meet because it has zero connection to what you do. Or watching people forget it immediately because there's nothing memorable about it except that it's short.

I wrote about this last week, but it bears repeating: a seven-letter name that people actually remember and can spell beats a random three-letter combination every single time. The goal isn't brevity for its own sake. The goal is making your brand stick in people's heads. If a slightly longer name does that better, use the longer name.

Short is a feature, not a strategy. Don't confuse the two.

Pretending .com doesn't matter

Look, I know there are alternatives now. .io became cool with tech startups. .ai is having its moment. .xyz exists for reasons I still don't fully understand. Some of these can work fine, especially early on when you're just getting traction.

But here's what actually happens: people will type .com anyway. Investors will type .com. Your own employees will type .com and end up on some parked page or worse, a competitor's site. I built RhythmGuitar.org as an affiliate site years ago, and I still catch myself typing .com out of pure muscle memory. It's embarrassing, but it proves the point.

You don't necessarily need to own the .com on day one, especially if it's $50K and you're bootstrapping. But you need a plan for getting it eventually. You need to know who owns it, what it would take to acquire it, and whether that's realistic. Ignoring it completely is just asking for problems down the road.

The .com bias is real, whether we like it or not. Factor that into your decision instead of pretending you can just skip it because extensions are "democratized" now or whatever.

Getting cute with spelling

Creative spellings seem clever when you're brainstorming at 2am and everything good is taken. "What if we spell it with a K instead of a C? What if we drop a vowel? What if we..."

Stop. Just stop.

If you have to spell your name out loud every single time you tell someone about your company, you've already lost. Word-of-mouth marketing—still one of the most powerful tools you have—becomes a nightmare when people can't figure out how to find you.

I've seen this play out so many times. Someone hears about your company at a conference. They're interested. They pull out their phone to look you up later and... they spell it wrong. They end up nowhere. You just lost a potential customer because you thought "Kwik" was clever.

Keep it simple. If your grandma can't spell it after hearing it once, it's too complicated.

Naming for version 1.0 instead of version 10.0

This might be the most expensive mistake on this list, and it's completely invisible until it's too late.

You build a tool for podcasters. You call it PodcastTool.com or VoiceEditor.io or something hyper-specific to your launch product. It fits perfectly. Everyone gets it immediately. Great.

Then six months later, you realize there's way more opportunity in video. Or you want to expand to all creator tools, not just podcasting. Or your best customers are using you for something you didn't even anticipate. And now you're stuck with a name that boxes you in.

Rebranding is possible, but it's painful and expensive and you lose momentum. Some companies pull it off. Most just live with the mismatch and let it slowly drain their brand equity.

Think bigger from the start. Your name should represent your vision, not just your MVP. Give yourself room to grow into it instead of immediately growing out of it.

The $10 domain budget (or: being cheap in the dumbest way possible)

Startups will burn $100K on Facebook ads or engineering salaries without blinking. But suggest spending five figures on a domain and suddenly everyone's clutching their pearls about fiscal responsibility.

This makes no sense. A domain is an asset. It holds value. If your company grows, it becomes more valuable. If things don't work out, you can probably sell it for most of what you paid. It's one of the few startup expenses that isn't purely a sunk cost.

I'm not saying every company needs to drop six figures on their domain. Most don't. But refusing to budget realistically for a good name because "domains should be cheap" is just... it's dumb. That's the only word for it.

Good names cost money because good names are scarce. You can either pay for quality now, or pay way more to upgrade later when you've built your entire brand around the mediocre option. Or worse, never upgrade and just accept the anchor around your neck forever.

Budget like an adult. Your domain is infrastructure, not a line item you skim on to save a few bucks.

Just don't be stupid about it

None of this is complicated. Don't chase metrics that don't matter. Don't ignore the extensions that do. Keep spelling straightforward. Think beyond your current product. And put some actual money behind getting a name that works.

The right domain won't make your startup succeed—plenty of companies with great domains have failed spectacularly. But the wrong domain can absolutely hold you back in ways you won't notice until it's too late to fix easily.

Take the time upfront to get this right. Future you will either thank you or curse you for this decision. Might as well make it the former.