If you have a unique business plan or web development idea that can’t easily or quickly be replicated, the domain name you choose for your website hardly matters. You can be CrazyCrazyCrazy.us or some other funky domain name, and you will still have success if there’s a strong market for your product or service. The domain name matters much less than the idea and execution.
If your idea isn’t completely unique or you are entering a market where there is considerable competition, the domain name can be critical to your company’s success or failure.
In just about every market, a new industry leader can emerge (or a new company can instantly be competitive) if he has the category killer domain name for the industry, as long as his product is at least competitive with the industry leaders. The company doesn’t necessarily need to be innovative to gain market share – just competitive.
New companies need to be innovative to take market share away from the leaders, or they need to spend considerable sums of money on marketing to get consumers to think its products are better or to give them a reason to buy them over its competitors products. A domain name doesn’t necessarily do all of this, but the category killer domain name does convey trust and is instantly recognizable.
Torah.com may not be the best looking website yet, as it’s a work in progress. However, I receive many Jewish-related questions every week from people who think Torah.com is the expert. I may not be from Lowell or have the most comprehensive site about Lowell (it’s debatable), but hundreds of people still visit Lowell.com each day, and many people book their hotel reservations right on the site.
A new company can spend a lot of money on marketing to convey trust. A category defining domain name can be expensive, but it can give instant credibility to a new or rebranded company.
Most of my domain purchases have come from either direct inquiries to domain owners after 
When you’re investing in a speculative domain name, keep in mind that you could have your money on the sidelines for a long time. If you are paying registration fee, it’s not a lot of money to worry about. However, if you buy dozens or hundreds of domain names at registration fee, or if you buy a domain name for a lot of money, it could be burdensome.
Some of the best domain names I have ever purchased came after receiving a notice with the subject “Delivery Status Notification (Failure)” meaning that it was not received by the intended recipient. This tells me that inquiries from others went unreceived as well, and acquisition attempts probably ended there (or a phone call, which generally goes to a non-working phone number). Without having received many offers, a domain owner may be more inclined to sell his domain name to me if I can just get in touch and make a fair offer.
I know a number of companies and individuals that have spent a lot of money buying domain names based strictly on revenue multiples, and there are many reasons why I think this is a bad idea. I personally have never bought a name strictly based on the amount of money it generates because of the reasons I outline below. I am sure there are plenty of people who have done well buying on multiples, with the “industry standard” previously being 10 years, but I strongly believe much more money has been spent on bad buys than good ones.