Definitely you shouldn't register domains in bad faith to exploit someone's pre-existing brand name. That would be cybersquatting, and it's prohibited. The UDRP can result in the domain being confiscated on that basis.

That said, just because someone uses a brand name similar to your domain does NOT mean that they necessarily have any right to own – or prevent others from using – that domain. It's commonplace to see many companies sharing similar or identical names. And when the domain registration predates someone else's usage of a name, that other person generally has no rights whatsoever to the domain.

Trademarks are tied to a (relatively small) field of usage. So many different companies might share the same brand name but use it in non-overlapping applications or jurisdictions. And in doing so, they generally don't violate one another's trademark rights. In fact, the USPTO (which governs trademarks in the USA) often grants trademarks to the same brand name to multiple different entities simultaneously.

If you're selling a domain name, then it is the BUYER who wil be using it. And it's that buyer's usage that determines whether the domain would violate someone else's trademark or not.

For example, if "Tooth Fairy" is the name of a dentist's office with a trademark filed already, and your buyer intends to use "Tooth Fairy" in the same way, then they will violate an existing trademark. But if they intend to use "Tooth Fairy" to brand a video game, then they will not.

Usage is the buyer's affair. It's beyond your control as the domain seller what the buyer will do with the domain.

That said, if you are registering domains that contain – let's say – "Google", then that's clearly bad faith. Only register domains where there are legitimate non-infringing uses possible or many divergent potential buyers, no single one of whom can lay sole claim to the domain.

It's impossible to answer your question without knowing some details about the "X" of your old domain and the differences between your old and new projects.

If X = BestHamburgersInLosAngeles.com. And your new project is sushi restaurant in Chicago, then you will need a new domain.

Does one (A) Pay more for the ideal domain name or (B) Save money by choosing a somewhat inferior domain name? It's a common question – so common that it probably deserves a name. The Entrepreneur's "Domain Dilemma", let's call it.

Of course, there are cases where the ideal domain really is too expensive. Asking prices can be crazy. And bootstrapping startups may have shoe-string budgets.

On the other hand, fair market prices for good domain names are higher than most people realize. Paying a few thousand dollars is average. And depending on the category of name, certain domains sell predictably within much higher price ranges: 5, 6 or 7 figures.

There is no single answer that will always be right – whether to buy the expensive ideal domain or to save money by going with a cheaper option. After all, this is the real world, which is about tradeoffs, about balancing pros and cons. Quality and Affordability – we sacrifice one for the other, almost inevitably, whenever we face any purchasing decision.

It's worth pointing out a few things. With an expensive domain name, you don't necessarily need to pay 100% of the asking price. I've helped clients negotiate less. And it's possible to arrange financing, leasing, and optioning contracts for premium domain names – with no obligation to continue paying if you decide (for whatever reason) to abandon the project or rebrand.

That can be really important for startups. Instead of starting with a name that LOOKS as cheap as your budget, you can start with the perfect name that reflects your future ambitions.
That better domain – the one you really want, not the knock-off second-rate version of your goal – can help you get eyeballs, look credible, achieve name recognition, and acquire not only clientele but possibly partners and investors. If your project succeeds, you can finish buying that perfect domain. If not, you can let it go after using it for awhile as an experiment and only paying a small fraction of that intimidating asking price. Conclusion: Sticker shock need not be fatal.

Also, keep in mind that – with almost everything in life – cutting corners might save money initially; but over time, such decisions often prove even more expensive. Like driving on worn-out tires. Or going to a job interview in sweat pants rather than buying that "superficial" suit.

People tend to underestimate this effect when it comes to domains because nobody shows up later to charge them an extra domain-related fee as a penalty for choosing a third-rate domain name earlier. Rather, the cost is indirect, hidden, if not invisible. But it's there.

The customers who forget your name (or the web address that is vaguely similar to your brand name) will google a generic description of what you offer. And so they'll run the gauntlet of your competitors, clicking on their sites instead of on yours. Better to get traffic via direct navigation through the browser.

Domains that contain extra words, or which don't exactly match your brand, or which are boobytrapped with non-standard suffixes (.CO instead of .COM, for instance) will lead to mistyped or misremembered attempts to reach you.
Not just in browsers. Emails will go astray and might be read by someone else.

Leakage due to a bad name is hard to detect because the people who WANT to find you ... don't. Ideally, your brand name and web address should be simple enough that one of your clients can refer you to their acquaintances over the phone with NO CHANCE that the other person will misunderstand, misspell, or forget that name / address a week or two later when they actually try to find you. If your brand / domain can't do this 100% of the time, then you are losing word-of-mouth growth. And you won't know it, but you'll have to compensate for it by extra marketing effort or expense somewhere else.

And if you are planning on someday upgrading to the better version of your domain – once you can afford it – that might cause complications. The owner of that domain might see your successful business and add an extra zero or two to the asking price. Or, perhaps even worse, a different startup might buy your ideal domain and use it for their own project. And whether they compete with you for customers or not, they WILL compete with you for rankings in Google, driving up your SEO costs (whether in dollars or time and effort).

The foregoing DOESN'T mean that you need to pay an exorbitant amount for your ideal domain. It only means that you should weigh ALL the pros and cons when making your decision about the tradeoffs.

Talk to me if you want a 2nd opinion from someone who has spent roughly a decade working full time on branding and the domain market. I've been in your shoes as an entrepreneur naming my own projects and buying (or not buying) my first-choice domains, depending on the particular case. And I've advised a lot of clients, helping them save money and end up with a name that provides better bang for their buck. Sometimes what appears to be your ideal domain isn't so ideal. Or else there might be other equally good domains that you haven't thought of, which might save you substantially.

Microsoft Word should do the trick. Such programs make it easy to outline anything you can imagine. Or any old piece of paper, really.

Fiction has been written well, generation after generation, long before anybody thought of "tools or platforms". Shakespeare and Hemingway never suffered unduly from lack of a convenient app.

A bad name will cost you money. How? Missed opportunities. I could list a dozen ways.

Changing a name will also cost you money. How? Time. Energy. Redesigning marketing materials. Etc.

I don't know whether your brand name / domain name is good or bad. But it sounds like you're dissatisfied with it.

Think of your brand name like a coworker. Either you "hire" a name that goes out of its way to build your brand and business. Or you "hire" a name that's lazy, doesn't show up, misplaces things, rubs customers the wrong way.

Interview your name before hiring it.

You can always share the fact that you found someone's advice helpful. Online, you can say something like this:

"If you're ever in need of [blank] advice, talk to [so and so]. They just helped me out with a question I had."

Where? If you have a blog, maybe add a random P.S. If there's a place to leave a review, consider that. Or if you're on social media, maybe share a thumb's up with people. They may not need any advice today, but maybe in a month or a year somebody will. Or maybe a stranger, searching online, will stumble across your thumb's up.

Naming your service based on your surname has some disadvantages. For example:

- Surnames aren't memorable. Personally I'm terrible at remembering people's names after meeting them.

- Surnames are sometimes hard to spell, which can lead to misdirected online traffic

- Difficult to separate yourself from the business. Your own name is your own reputation. Best to have a way to separate the 2 in case the business gets negative reviews. Or in case you later choose to to be known for something else.

- What if you want to sell the company? Do you want your personal name attached to somebody else's business practices? Meanwhile, if the buyer is thinking about rebranding, then they'll plan on deducting that cost from what they'd have otherwise paid you.

If you'd like more advice on naming and/or domain selection, let's set up a call. These topics have been my full time job for years.

Asking other people to give us their products and labor for free ISN'T normal. So when someone asks us to give up our time or property for their benefit, we really must push back – even if only with a raised eyebrow.

Sure, in charity cases, we might be generous. And there might be a few startups where the risk / reward analysis justifies sweating out a contribution for the sake of equity alone. But wantrepreneurs are a dime a dozen. Something like 90% of them fail. So the bar needs to be high.

You understand this already. But do the panhandler CEO a favor and explain the situation to him as well.

Just because someone fancies himself an entrepreneur doesn't mean his daydreams are a credit card with an infinite limit. Would he tell his landlord to accept equity instead of last month's rent? Would he wave away the waiter at the restaurant, saying, "Congratulations! You own 0.1% of my latest startup fantasy"? Would he approach a used car salesman and volunteer to pay with stock in a mirage?

No self-styled entrepreneur would dare do any of those things. He'd feel sheepish to the point of paralysis. Yet, illogically, many wantrapreneurs feel that it's somehow appropriate not just to ask but to EXPECT web designers, app developers, and the like to give up their own projects and work for them for free – i.e. for a 90% chance of the equity being worthless.

Once you sit the person down and explain these facts, they'll usually understand.

People don't value what they don't pay for or work for or make sacrifices for. If the entrepreneur is eating out at restaurants, watching TV in the evening, or taking Saturday off, then he has no right to expect you to go unpaid while he's luxuriating in indolence. Let him make his own sandwiches for a month and divert his free time into an evening or weekend job and pay you that way. Then he'll understand what it means to ask someone else to work for nothing.

If the entrepreneur really can't afford to pay you, then BARTER is the fair way to proceed. Not with equity. His startup idea is probably a mirage; and, statistically speaking, is likely to flop. Find something he owns or can provide that you can benefit from. Make a swap. Or if you're just too busy to work on another unpaid project, tell him.

Figure out a website you yourself would like to manage as a business or hobby. Choose something just complex enough to show off your skills ... but not something so ambitious that it would eat up all your time.

Then pick the best domain name for the project you can reasonably afford, and get started. This will be good practice – not only for the sake of honing your dev skills, but also for understanding the challenges of designing a website, furnishing content, attracting customers / readers, monetizing traffic, and so forth.

These are the very challenges your employers or clients will be facing. If you understand their perspective, then this helps you help them; and it helps them trust you to help.

If you can spare 5 minutes for a consulting session, I have several ideas for promoting a blog related to tall menswear specifically.