- Allison Ko
- 2 hours ago
- 12 min read
Get started: Create a website → | Get a domain →
Nobody really talks about how tricky it can be to choose a domain name for your website.
The truth is, many of us get stuck at this part—but hardly anyone admits it. Even though we’ve all been told that “there’s no such thing as a stupid question,” most of us are too embarrassed to ask basic questions like: how do domains actually work, and how do you know if you’re making the right choice?
So, today, we’re going to address the elephant(s) in the room. We asked business owners, “What question about website domains did you hesitate to ask when you were first starting out? How would you answer them today?”
Here are the top questions they recall having and their advice for people who find themselves in their shoes today.
01. Why does a domain name matter?
“One question I hesitated to ask was, Does my domain name really matter?” admits Amore Philip, director of public relations for Apples & Oranges Public Relations. In retrospect, “the answer is a resounding yes; it absolutely matters. Your domain name is often the first impression people have of your business.”
Co-founder of Reclaim247, Andrew Franks, agrees: “At the time, [the emphasis on domains] seemed a little shallow. I thought, ‘Clients were going to evaluate us based on results, not on the couple of words in a URL.’ I didn't appreciate the impact of the domain on first impressions, perceived credibility or even how likely someone is to refer you to a friend.
“In hindsight, I would make the choice of a domain an actual decision. After all, this is the label under which many of your customers will first find you.”
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02. When should I invest in purchasing a domain?
When you’re creating a website, the obvious move is to grab a domain once you’re ready to go live. But business owners like Joseph Depena found that the better move is to do it even earlier.
“As a franchise owner, I launched VP Fitness in 2011 and transformed it into a successful franchise by 2023. My biggest hesitation regarding domains was whether to secure franchise-related domains before I was actually ready to franchise.
I waited until 2022 to acquire franchising.vpfitness.net, thinking it was premature. That was a mistake—by then, I had to pay premium prices for related domains and missed early SEO opportunities. When we officially launched franchising in 2023, competitors had already claimed similar domain variations in the fitness space.”
Similarly, Brandon Brown, CEO of Search Party, recalls, “Early on, I hesitated to ask if I really needed to secure domains for product extensions before we even announced them. Looking back, the answer is yes—competitors pick up on signals faster than you expect, and opportunists don't hesitate to grab them…I now keep a simple rule: If there's even a 20% chance a new product name could stick, I grab the domain right away. It's inexpensive insurance that saves you from a headache later.”
03. Should I buy multiple domains for my website?
“When I started Plasthetix, I didn't ask if I should lock down multiple variations of my main domain, and I underestimated how much confusion it could save later,” says Josiah Lipsmeyer, founder of Plasthetix Plastic Surgery Marketing. “Patients would sometimes type in a slightly different spelling and end up on competitor sites. I wish I'd thought earlier about protecting variations and redirecting everything cleanly to one hub…it's one of those simple moves that feels unnecessary until it isn't.”
“I thought it seemed paranoid and expensive to buy multiple domain variations,” remembers Lori Appleman, co-founder of Redline Minds. “That hesitation cost one of my early clients dearly. A competitor bought the .net version of their .com domain and created a nearly identical site. Customers got confused, and my client lost about 15% of their direct traffic over six months before we caught it.
Now I always tell store owners to secure at least the .com, .net and common misspellings of their domain upfront. It's cheaper than fighting for traffic later. One client spent $200 protecting their brand initially, versus the $3,000 they would've paid trying to buy back domains from competitors.”
“The answer is balance,” adds CEO of SonderCare, Kyle Sobko. “Keep the main name and then spend an extra $40 or so on the most obvious typos or extensions. Anything more should only be bought if you are launching a new product or entering a new country. Otherwise, you risk spending money that will never return value."
04. What makes a good domain name?
While almost everyone agrees that there isn’t a once-size-fits-all formula for a good domain name, many attest to spending countless hours debating on the length, scope and “literal-ness” of their domain name.
Ladina Schöpf, co-founder of Building Green Show, elaborates further, “When I first started, I wasn't sure if my domain name should show my brand's purpose or be short and easy to remember. I was worried about making things too complicated, but looking back, that's exactly what I should have been asking. Now, my advice is to pick a domain that does both. For us, buildinggreenshow.com quickly tells people what we do while being simple enough for them to recall and share.”
Co-founder of Kontra, Jan Kawecki, chimes in saying, “I didn't ask myself the question of ‘Does the domain name sound good?’ because I thought that's a silly question and nobody really asks that. Only later did I realize how many people would compliment my domain, saying that it sounds really good, and it’s easy to pronounce.
“Now, I’d suggest asking yourself questions like, will someone who is not familiar with my website be able to pronounce it? Will they be able to remember the name and recognize it later? Finally, will it sound natural in other languages? If the answers to these questions are ‘yes,’ then you're looking at a good domain name that will serve you well.”
Read also: Should you choose a niche-focused domain?
Founder of eLearning Industry Inc, Christopher Pappas, points out another key factor: "In the beginning, I did not fully consider how our domain name would influence our social media presence. I was focused on getting the website up and running, assuming that the domain alone would be enough.
“However, over time, I realized the importance of consistency between our domain and social media handles. Having a unified approach across all platforms not only makes it easier for customers to find us, but also strengthens our brand recognition. I now recommend aligning your domain with your social media handles, as it has proven to be a powerful tool for brand consistency.”
Need help thinking of a good name? Try Wix’s free domain name generator.
05. Should my domain include keywords?
The relationship between domains and SEO has been under the microscope for a while now. But, according to Allison Andrews, director of sales and marketing for Limitless Limo, the answer to this question depends on how your customers search for companies like yours.
“My biggest domain hesitation was whether to include ‘limo’ in our URL when we offer so much more than just limousines,” she says. “Turns out keeping ‘limo’ was brilliant for SEO. When brides search ‘wedding limo Columbus’ or executives need ‘airport limo near me, we dominate those searches. Our limitless-limo.com domain pulls in 40% more organic traffic than competitors with generic names like ‘luxurytransport’ or ‘premiererides.’”
In many cases, SEO shouldn’t be the end-all-be-all factor, notes Dr. Chad Walding, chief culture officer and co-founder of NativePath.
“My most significant area of failure was nearly the ruin of my business,” he reflects. “I wasted three weeks being obsessed with the idea of naturalhealthsupplements.com because all experts in the field of SEO said that keyword domains were better placed. I constantly doubted myself when I decided to use nativepath.com since everybody was putting keywords in their web addresses.
“[But going with a more branded domain] rescued my company. Our small, easy-to-remember domain is now promoting more through word of mouth than any actual advertisement would."
06. Are premium domains worth it?
The “perfect” domain looks different for everyone—and if you’re lucky, the one you want isn’t too expensive or hard to snag. For those chasing a more coveted domain, though, this dilemma is all too familiar.
Speaking from his own experience, Baris Zeren, CEO of BookYourData, can confidently say that there are instances when a domain is worth the high price tag.
“I was afraid to ask whether I should spend $8,000 on the exact domain match when I barely had enough capital to get through the first three months of operations,” he says. “I didn't ask because everyone around me seemed to have their domain strategy down cold, and I didn't want to look stupid.
“Today I would answer that the domain is worth the cost, and I would have saved myself from 40% of serious client conversations, had I invested extra cash back then for a better domain. Decision makers for larger companies automatically dismiss vendors with awkward or hyphenated web addresses before they even have a chance to see what you really offer.”
Gregg Feinerman, owner and medical director of Feinerman Vision, shares this sentiment: “When I began my practice, I was afraid to ask whether I had made the right decision of spending almost $1,000 on a domain with my own name. Most of my colleagues settled on generic medical words below $50, and I felt that I was paying excessively at the time.
“That decision has been paid back many times over in the years since. Nearly 70% of my new patients report researching me by name prior to booking…A domain must be considered as a permanent investment, just like sophisticated equipment or employee education. It develops as you grow in your profession, rather than becoming obsolete as services evolve.”
07. Should I consider alternative domain extensions?
"When I was starting out, I didn't dare ask if I'd made a mistake not getting a .com,” shares Amy Bos, co-founder and COO of Mediumchat Group. “It felt like an obvious rule everyone else already knew: real businesses use .com, the rest make do.
“Looking back, I see that was nonsense. Yes, .com still carries weight because people instinctively type it, but it's not the make-or-break factor I thought it was. What matters more is whether people can remember your domain and trust it enough to click.”
In some industries, alternate TLDs can even give you an edge, according to Runbo Li, CEO of Magic Hour. “Today, I'd confidently say: yes, the extension you pick matters—but not always how you think. We embraced a .studio domain, and it helped position our brand as creative, modern, and niche-specific from day one.”
Still, some business owners are strong believers of .com.
“As a CPA who's helped hundreds of businesses across tech, property management, and professional services over more than 15 years, the domain question I wish I'd addressed earlier with clients is: ‘Should I buy the .com even if my LLC name doesn't match exactly?’” says Michael J. Spitz, principal of Spitz CPA.
“One of my AdTech clients lost thousands in misdirected traffic because customers kept typing their brand with .com instead of .co. The financial impact is real—I track this in client cash flow models. That same client eventually bought the .com for $3,200 from a domain squatter, money that could've gone toward inventory or payroll.
“Now I tell every new business formation client: secure the .com first, then structure your LLC name around what's available. From a tax perspective, domain purchases are fully deductible business expenses in year one. But the opportunity cost of the wrong domain choice compounds monthly through lost revenue."
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08. Should I consider subfolders and/or subdomains?
Founder and managing director of All Marketing Services, Alex Lloro, still remembers thinking, "Should I use a subdomain or a subfolder for my content? I hesitated to ask because I didn't understand the difference fully and didn't know the consequences.”
“Unfortunately, I learned the hard way,” Alex continues. “Our articles were on our subdomain for the first six months because it was easier. Our blog posts got traffic, yet our service pages were flat. I hired a team and realized the domain authority we were building wasn't flowing into the main site.
We were forced to migrate to a subfolder [that would make sure that all the SEO equity flows into your main domain]. The redirects, traffic dips and indexing issues during the migration were inconvenient and expensive. Fortunately, our blog and service page rankings got better after the switch.”
Owner of Stout Tent, Caitlyn Stout, shares a similar thought: “I wish I'd also asked about subdomain strategy from day one. When we launched our Glamping Business Blueprint course, we had to retrofit our site structure. Planning for product expansion in your domain architecture saves massive headaches when you're generating multi-million dollar revenue streams.”
09. Do domain age and history matter?
"In the beginning, my biggest mistake was thinking anything went, as long as the domain was clean, and the name matched the brand,” says managing director of SEO Gold Coast, Sean Clancy. “I did not ask if a domain's history matters because I thought at that point that Google treated fresh projects the same way, regardless of history.
“A few years later, I learned some domains come with baggage. If a domain has a history with spammy link networks or has been de-indexed, it can take months for you to signal any trust before you can actually gain some traction.”
“Old domains can give an advantage—if they have a good history, quality backlinks, and no spam or penalties,” agrees Alexey Karnaukh, co-founder of LinkBuilder. “We once bought a domain with a strong history, but due to hidden spam links from the past, the site had a hard time getting to the top. So now I would say, if you take an old domain, do a full audit; check it in the Wayback Machine, look at the backlinks in Ahrefs and make sure that there were no bans in Google.”
10. Should I invest in domain privacy protection?
Most domain registrars offer privacy protection, but like many first-time site owners, you might be wondering if it’s worth the extra cost. That’s the question that Leon Huang, CEO of RapidDirect, had early on.
“I sadly assumed I wouldn't need domain privacy when I first started my business, as it was my business information, not my personal information, that I used to register the site,” Leon explains. “But without it, your contact information is publicly listed, which opens you up to a flood of spam and unwanted business solicitations. I made the mistake of skipping it when I first registered our domain in 2012, and my phone was flooded with spammy sales calls for weeks.
“Scammers and social engineers also actively scrape this public data to help create convincing phishing emails to attempt to trick your team into paying a fake bill or clicking on a malicious link. With domain privacy, they no longer have easy access to that information.”
“Back then, I thought basic registration was enough,” adds Joseph Passalacqua, owner and CEO of Maid Sailors. “Now I always set domain-lock, add two-factor authentication on my registrar login and turn on WHOIS privacy. By adding those safeguards, I've reduced the risk of hijacking or forced transfers and kept control of the main gateway to my business online.”
11. What do I need to know before registering my domain?
Domain registration should be straightforward, and yet, oftentimes it’s not. For many business owners, there are a plethora of mistakes they could’ve avoided if they had known what questions to ask.
“I should’ve asked, ‘What is my domain's exposure to external risks?’” says Daniel Yeromka, CEO of HostZealot. “A domain seems like a simple thing that you buy and forget. I didn't know that domain registrars might get acquired, or that there might be regulatory changes around domain ownership and enforcement. I was also unaware of the risks of disputes—trademark claims, cyber squatting and domain hijacks.
“[If I could do things over now,] I would look at the registrar's stability, their registry policies and any trademark overlaps. I'd even test my exit strategy and see how fast it would take to transfer my domain if anything happened."
Owner of Keystone Technology Consultants, Brian Fontanella, additionally points out, "Early in my career, I overlooked an important question: What if I do not own my domain? I assumed that paying for website setup meant full control, but that was not the case.
“A local marketing agency registered the domain under their name, not mine. I only discovered this when I tried to change providers and realized they controlled access to my account. Negotiating for something I believed I owned was challenging, and that lesson has stayed with me.
“Now, I advise business owners to ensure their business is listed as the domain registrant and that they retain all login credentials. This may seem straightforward, but many companies unknowingly give up control.”
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12. Can I change my domain?
“One of the basic questions I had was about changing our domain name in the future. If I wanted to rebrand, add new products or just go with a cheaper domain name, how would that work?” says Jonathan Palley, CEO of QR Codes Unlimited. “I've learned a lot about web architecture since then, but it's still a basic question that I get a lot from my colleagues who are launching their own businesses.”
Further reading: How to change a domain name
“I avoided asking whether changing domains later would destroy SEO progress. Fear of the answer kept me silent,” admits Jason Hennessey, CEO of Hennessey Digital. “Eventually, we had to migrate a client's domain…We guided that client through meticulous domain redirects, technical audits and communication campaigns. Traffic dipped briefly but recovered within months. If they had asked earlier, anxiety could have been reduced. Domain transitions are survivable when managed strategically. Hesitation often creates unnecessary stress."
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