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Domain nightmares: 23 business owners share their worst naming mistakes

Updated: 5 days ago


Domain nightmares: 23 business owners share their worst naming mistakes

When you’re creating a website, you’d assume choosing a domain name would be the easy part. But as many of us know, it’s harder than it looks—and oftentimes, hindsight is 20/20. 


We recently asked business owners: What’s one mistake you regret making when choosing a domain name for your site?


Turns out, there are many things that can go sideways when starting a business with the wrong domain.


Here are the top mistakes that business owners vow to never make again. Keep reading for their tips on how to avoid making them yourself.




Top domain naming mistakes, according to real business owners:




01. Picking a name that’s too similar to a competitor’s 


"When I created my first site on Wix, I made the mistake of picking a domain without doing proper SEO research,” says Olivia Chiavegato, founder and CMO of The Vitalist. It wasn’t until her site went live that she found out a French winery had a similar name—and already dominated the first 12 pages of search results. 


“No amount of SEO optimization was ever going to help me get that first result,” she adds. “Fortunately, I spent time carefully thinking and researching other names before finding a new domain name that had very little relative competition.” 



quote about making a mistake of picking a domain without SEO research


Similarly, Edward White, head of growth at beehiiv recalls how “a friend of mine launched a startup and originally chose a name that was different, but slightly similar to a well-funded industry leader's name. They stuck with it for a short time, but mix-ups were happening often, and every dollar they spent on brand-awareness ads had a spillover effect. Instead of 100% of their ad investment going to boost their visibility, they were also inadvertently boosting their competitor's recognition.


“The biggest issue was the unwinnable SEO battle…He eventually pivoted, but it caused a lot of unnecessary pain. [So before you commit to your URL,] audit the entire competitive landscape for names that are phonetically similar or close in spelling. If you find yourself having to explain, ‘No, we're the one without the S at the end,’ you've already lost.”


Related reading:



02. Choosing creativity over clarity 


There’s a fine balance between creativity and clarity. But almost everyone agrees that clarity always comes first. 


“A name that's easy to say, spell and remember beats a ‘cool’ one every time,” says Borets Stamenov, co-founder and CEO of SeekFast. "We picked a clever, short domain that no one could spell right. It looked great on paper, but every time we said it out loud, we had to follow up with ‘That's with a K, not a C’ or ‘Two Ls, one Z.’ We lost traffic, emails bounced and worse—people Googled the wrong thing and found competitors.” 


Stella Morrison, founder of The Stellastra Effect, also notes, "One big mistake I see clients make when selecting a URL is opting for abbreviations or shortened words that aren't easily identifiable.


“For example, a company called All Things Fans might use their full name across all their branding, but choose the URL ATFFans.com [because it’s available and cheaper than AllThingsFans.com]... Naturally, people are going to try AllThingsFans.com first, and when there’s nothing there, customers will assume All Things Fans was out of business.”


Stella recommends staying true to the name your business uses publicly. And only if needed, explore options like ShopAllThingsFans.com or an alternate TLD like AllThingsFans.store. 



03. Not considering geographic differences 


Seven years ago, when Jake Bunston, owner of MAKE Fencing, was creating his domain, he almost went with MelbourneFencingContractorsSpecialists.com. 


“Thank god I didn't pull the trigger on that monster,” he says today. “The real issue wasn't just length—it was industry confusion. In Australia, ‘fencing’ can mean sword fighting, which led to some awkward phone calls early on…What saved me was keeping it simple with MakeFencing.com.au. People remember ‘make’ and know exactly what we do.”


Like Jake, insurance expert, Eamonn Turley, also reaped the benefits of localizing his domain name. “One mistake I made early on was choosing a domain that wasn't quite right for our audience and market,” he says. “We originally launched with a .com domain, thinking it would give us more credibility and international appeal. But over time, we realized that the majority of our customers were based in the UK and felt more comfortable engaging with a business that had a local identity. 


“Eventually, we made the decision to switch from multiquotetime.com to multiquotetime.co.uk, and redirected all traffic accordingly. As soon as we did, we saw a noticeable increase in traffic and engagement from UK users.”


It was a different story, however, for Joseph Lopez and his mobile IV therapy company, Arizona IV Medics LLC. “As our business grew, that domain became a ceiling rather than a foundation. The problem hit hard when we started getting calls from clients in neighboring states who wanted our services…We lost at least 40+ potential clients in our first year just from this perception barrier.


“What really drove the lesson home was when a major hotel chain reached out about partnering across multiple southwestern states. During negotiations, they specifically mentioned that our ‘AZ’ branding made them question our ability to scale beyond Arizona borders. That conversation cost us a six-figure partnership opportunity.


“If I could do it over, I'd choose something like IVMedicsUSA.com or create a completely brandable name that doesn't lock us into geographic limitations. Your domain should grow with your vision, not constrain it.”




04. Picking a name that’s too long and fails the ‘phone test’


Simple is best. That’s what Courtney Epps, owner of OTB Tax, had to learn the hard way.


“My biggest mistake was initially considering TaxStrategySouthCarolinaAccounting.com because I thought cramming my location and services would help people find me. The wake-up call came when a $2M client couldn't remember how to spell out my long domain during a phone referral to his business partner. I realized that 90% of my referrals happen through word-of-mouth conversations, and people need to instantly recall and share your web address.


“Our current URL, OTBTax.com, works because it's short, memorable, and reflects our ‘Outside The Box’ approach without being literal.”


Courtney recommends testing any domain by saying it out loud to someone when they're distracted, then asking them to repeat it back 10 minutes later. If they can't spell it perfectly, then it’s not worth it. 


Founder and CEO of Scale Lite, Keaton Kay, is on the same page. “I've worked with hundreds of service businesses through my private equity background, and one domain mistake cost a client over $80,000 in lost revenue. A Denver water restoration company had ColoradoWaterDamageEmergencyServices.com—38 characters that nobody could remember during actual emergencies. When people had flooded basements at 2 a.m., they'd Google ‘water damage Denver’ instead of trying to recall that massive domain…


“The killer was their truck wraps and business cards. The domain was so long it had to be printed in tiny font…After switching to a 12-character .com, their direct traffic jumped 40% within three months.”



advice on creating a long domain name


05. Neglecting SEO research 


It used to be said that the best domains are those that include relevant keywords. Today, exact-match keywords may play little-to-no role in your search rankings. 


Take the name BestDigitalMarketingServices.com as an example. According to ZontSound’s founder and chief technology officer, Nikolay Petrov, “I had a friend use a name like this for his startup, hoping it would help him rank more quickly in SERPs. And it did...initially. But his domain sounded very generic and forgettable, like a commodity rather than a brand. It didn't leave any room for him to expand past one small niche, and it wasn't the kind of credible, emotional connection you can forge with a good brand name.”


He advises to focus on building your brand, even if it takes time. “A great website builder gives you enough control over layout and SEO that you don't necessarily need your domain name to rank (at all).”


Favour Obasi-ike, project scheduler and host of We Don’t PLAY! podcast, knows the impact that this strategy can have.  


"I chose a domain that didn't match how people actually search for my services. My company name (Work & PLAY) suggests entertainment and music, when I primarily offer digital marketing and SEO services…so people initially struggled to find my business website because they'd search things like ‘SEO services’ instead of my actual company name.


“What saved me was creating content that bridges this gap. I now optimize every blog post and podcast episode with the keywords my audience actually uses when searching for solutions.” 



06. Ignoring potential trademark issues 


When creativity strikes, it's easy to forget one important step: checking for trademarks.


“I've seen business owners fall in love with a domain name, buy it, build the brand around it—and then get hit with a cease and desist,” says Scott Gabdullin, Learo’s CEO and founder. “Not only is it a legal headache, but it can tank your SEO, confuse your audience and force an expensive rebrand.”



advice on checking trademark issues before picking a domain


"I once registered a premium domain for an online tool with high search volume,” chimes in Burak Özdemir, founder of Online Alarm Kur. “After experiencing the high of getting it, I wondered why I was able to get it so cheap. A few searches later, I found out a company had launched a big business on the same domain for the same purpose a few years earlier, but had since shut it down. 


“My gut told me to check if the wordmark was registered at the USPTO and, sure enough, it was. A parallel filing was at the EUIPO too. Overnight, the perfect address became a sinkhole. Trademarks are no joke. Anyone registering a domain should first search the trademark databases, then register the domain, not the other way around as I did."




07. Ignoring domain reputation


Before purchasing a domain, remember that it could’ve once belonged to someone else. 


For example, in Emily Ruby’s line of work, it’s common for businesses to use similar-sounding names. When her law firm, Greenberg and Ruby Injury Attorneys, was on the hunt for a URL, she recalls a situation in which a colleague found a seemingly perfect name and jumped to purchase it.


“Unfortunately, he never investigated its past life before purchasing it,” she says. “The first sign that something was wrong was when his initial marketing emails had a shockingly high bounce rate. He later found out the domain was on several major spam blacklists because of bad behavior from the owners before him."


Emily mentions that the site was also completely invisible on search engines. After running g a backlink analysis, the team found that the domain had thousands of low-quality, toxic backlinks pointing to it because the previous owner had opted for black-hat SEO tactics. Search engines had effectively blacklisted it, too.


“The fix entailed a painful and time-consuming process of requesting removal from email blacklists and rejecting toxic backlinks, but the damage was already done," she recalls. "Always run a domain's history through the Wayback Machine and backlink checkers before you buy it. A premium name with a toxic past is worse than a slightly less perfect name with a clean slate.”




08. Ignoring semantic associations


How we understand a turn of phrase—or even simple statements—can sound different to someone else. That’s why it’s important to test your domain in front of real customers before committing, advises content creator Sonny Da Badger.  


Sonny elaborates, “I've been running Support Bikers for years and made the classic mistake of assuming bikers would automatically understand what we do from hearing the name supportbikers.com. It sounds clear to us, but I learned that many people assumed we were just another charity or advocacy group rather than a business directory.


“The real wake-up call came when people would mention they’d admit they'd seen our site but clicked away thinking it was just about biker rights. We were losing potential users because our domain didn't immediately scream ‘find motorcycles here.’”


Cary Byrd, founder of CinchLocal, also reminds us not to forget about how automated systems may interpret words. This is especially true for businesses in regulated industries like healthcare, finance or pharmaceuticals. 


“I've been running digital marketing companies for over a decade, and the biggest domain mistake I made was with my first venture, eDrugSearch.com,” Cary notes. “It created massive problems with email deliverability and advertising platforms that automatically flagged anything with ‘drug’ in the URL.


“We lost thousands in potential revenue because our business emails went straight to spam folders, and Google Ads repeatedly suspended our account for policy violations, even though we were helping people find legitimate prescription medications from licensed pharmacies.”



09. Using hyphens


Believe it or not, this little punctuation mark can cause a lot of trouble. 


CEO of ServerMonkey, Bashar Hindi, recalls that “when we first launched ServerMonkey, we made a rookie mistake with our domain name. We thought being creative would set us apart, so we chose a quirky, stylized name that included a hyphen and a vague term. It felt fun and unique at the time, but looking back, it was a usability nightmare.


“Customers struggled to remember the exact name and often mistyped the URL. Worse, sending out email addresses with a hyphen caused endless confusion. It wasn't until we shifted to servermonkey.com that things started flowing smoothly. The difference was night and day in terms of web traffic and overall brand recognition.”



10. Boxing yourself in by only thinking about the short term


The best domains are scalable. 


“After 25 years in eCommerce, I've seen countless store owners pick domains that sound like product catalogs instead of brands,” states co-founder of Redline Minds, Lori Appleman. “They choose domains that describe what they sell today instead of building a brand for tomorrow…and though a descriptive domain might seem logical initially, it becomes a liability as you grow.”


“One mistake I made early on was choosing a domain that matched my LLC name exactly,” admits Lisa Martinez, who founded TX Cash Home Buyers. “At the time, it seemed like the right choice, but looking back, my LLC name just wasn't very catchy or brandable. I ended up creating a DBA (Doing Business As) and building my brand around that instead.”



advice on picking a brandable domain


At the same time, as you’re future-proofing your domain, avoid some classic mistakes like securing multiple domain variations without considering the user experience. 


“When I launched Rocket Alumni Solutions, I secured multiple domain variations, thinking I was being strategic [and preventing competitors from taking similar names]. We had walloffame.us, touchhalloffame.us and halloffamewall.com all pointing to the same product,” says founder and CEO, Chase McKee.


“The reality was brutal during our early sales calls. Prospects would visit one domain, then later search for us using a different variation, creating massive confusion about whether they were looking at the same company. Our support team started getting tickets asking why our ‘different websites’ had conflicting information."


The breaking point, he notes, came when a school district’s procurement team almost disqualified them because they couldn’t figure out which website was actually theirs during the vendor verification process.


"We were literally competing against ourselves...After that, I learned to pick one primary domain and stick with it religiously across all marketing materials. Our close rate jumped from 30% to 40% partly because prospects weren't second-guessing whether they were on the right website.”



11. Failing to check name availability across other platforms 


Your domain name doesn’t live in isolation. In fact, “choosing a domain is only step one,” says James Bowers II, chief security and compliance architect at Input Output


He adds, “If that same name—or even a close variation—is already taken on social media platforms like Instagram, X, LinkedIn or YouTube, you've just created a branding nightmare. We've seen businesses invest in a domain only to realize too late that their handle on major platforms is taken or worse, associated with unrelated (or questionable) content.”



12. Picking the wrong domain extension


Outside of the most popular .com extension, there are many other types of domains to choose from these days. You’ve got .co, .shop and .online (among others). While they each have their own strengths, picking the wrong one for your industry or for the wrong reasons can come with its consequences. 


“Years ago, a client registered a .io domain because their preferred .com wasn't available. It felt like a modern alternative at that time, and they didn't think twice,” mentions Matt Bowman, founder of Thrive Local. “They had no idea .io was tied to a specific country. The business wasn't connected to that region at all but search engines assumed the site was meant for that location. That one decision ended up hurting their visibility in the markets they actually wanted to reach.”


In a similar vein, Apoorva Govind, CEO and founder of AI ad generator Bestever, shares, “When AI was first introduced, we chose an .ai domain. It helped people understand what we offered and it was quite trendy—but it turned out to be a double-edged sword. 


“Many corporate entities were completely against AI adoption and even blocked .ai domains on their networks, seeing them as a higher risk for spam. This made it difficult for us to reach them, our potential clients, and even caused issues with email deliverability. Having that .ai domain put us in the same category as hundreds of low-quality AI tools, making it a lot more difficult to prove our worth.”


A word to the wise: avoid picking a unique TLD just because it’s trendy. Research the competitive landscape and understand both the risks and benefits before making a final decision.


See also: 


What to avoid when picking a domain

Example

Picking a name that’s too similar to a competitor’s

A startup calls itself Netflikz.com hoping to ride on Netflix’s popularity—confusing customers and inviting legal trouble.

Neglecting SEO research

A wellness blog uses the domain ZenVibesDaily.com, not realizing “zen vibes” has almost no search traffic, while “meditation tips” does.

Choosing creativity over clarity

A tech review site chooses Sproxxly.com—unique, but no one can spell or remember it, and it's not clear what the site is about.

Not considering geographic differences

A UK-based real estate agency uses FlatFinder.com, but U.S. audiences search for “apartment” instead of “flat.”

Picking a name that’s too long and fails the ‘phone test’

A local bakery uses SweetTreatsandDeliciousDelights.com, which is great on paper, but is hard to relay over the phone without errors.

Ignoring potential trademark issues

A software company launches under SnapSoft.com, then gets a cease-and-desist from Snap Inc. over trademark infringement.

Ignoring domain reputation

A brand buys GreenEnergyPro.com without checking that it was previously used for spammy affiliate schemes, hurting email deliverability.

Ignoring semantic associations

A travel booking site calls itself CrashTrip.com, unintentionally evoking accidents and negative travel experiences.

Using hyphens

A clothing brand goes with Cool-Threads.com—but most people forget the hyphen and end up on CoolThreads.com, a competitor’s site.

Boxing yourself in by only thinking about the short term

A site named BuyElectricScootersNow.com does well initially, but struggles to pivot when it expands into e-bikes and other mobility products.

Failing to check name availability across other platforms

A podcast registers DeepDiveTalks.com, but can't get @DeepDiveTalks on Instagram, TikTok or Twitter, which are all already taken.

Picking the wrong domain extension

A U.S.-focused tech company uses TechWizard.io, but many users assume it’s .com, leading to misdirected traffic and lost credibility.


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