Does it make sense to buy multiple domain names?

Does it make sense to buy multiple similarly-sounding domain names to redirect to your site?

Nope. 

There is scant data to support the business case for buying or leasing additional, similarly-sounding URLs and redirecting them to your existing site. This activity does not improve your search ranking on Google. The only possible benefit is if someone were to actually type the URL into the address bar. And, people don't really do that, anymore. They click on links: links in Google, links on Facebook, links in an email, etc. If the link is broken, they immediately lose interest and move onto the next Facebook post (or whatever).

I believe your money would better be spent on web ads: Google Adwords, banner ads in the local paper, and Facebook.

The only two exceptions I can think of:

1. if you are running a behemoth of a campaign - like a presidential campaign. In that case, you definitely want to get the .org and .net, and also get permutations of the candidates name (hilaryclinton.com and hillaryclinton.com - with one and with two Ls). 

2. If you are running a business, pick up anything related that might someday become the URL of a competitor. 

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Tim Wayne - NationBuilder Consulting - Interaction Design

Here's what my clients say:

"Tim has been a great asset to the Educate Our State team not only developing a beautiful, easy to manage and highly functional website but also offering guidance on social media best practices and strategic planning for our future on-line presence. Tim's ability to quickly navigate issues, consider various solutions and support our team through a number of phases of growth has been remarkable. His get-it-down attitude and quick responses have made this piece of our communications platform easy to build and launch. We can't recommend Tim highly enough!"
Crystal Brown, President, Educate Our State

"Tim has the most amazing talent, he can nearly read your mind and then improve on your idea... He should be on the TV show Heroes, because if you give him copy and some direction he comes back with what you had in mind but even better."
Jim Ross, Jim Ross Consulting

"Tim built our website quickly and beautifully. It represented our business and our service to clients well. The professional image he created for us was an important part of our success."
David Schachter, Lead Analytics Engineer at Playdom

"Tim was a pleasure to work with; he provided valuable expertise in a timely manner for a fair price. What more can you ask for? I hope to have the occasion to work with him again soon."
Mir Haynes, CEO, Anabo Studios

"I love working with Tim Wayne!
Tim is creative yet practical, balancing his keen design sense with an appreciation for real-world business considerations. Tim takes instruction well, though he requires little.
Bottom line: Tim always produces first-rate designs that are appropriate to a website's message and market--and he's fun to work with, too!"

Lang Zerner, President, Studio32

"Tim is a great web designer who, when given the chance, can come up with some pretty amazing stuff. His eye for design and all things aesthetic never ceases to amaze me."
Tony Chang, Senior Engineer, ServePath

"Tim is a very thorough and detail-oriented designer. He is an asset to the integrity of our three brand's commercial websites."
Liz Dizon

"When I worked with Tim, I immediately recognized what an awesome person he was. He helped our group design all of ServePath's customer sites. What made Tim invaluable was that he understood the mission and business objectives clearly. Based on the these, he architected sites that were able to draw in a substantial amount of customers, with compelling content, easy navigation, rapid product fulfillment, and order processing. This allowed customers to quickly and efficiently complete the transaction of their service and begin operating immediately.

As a sales person, I worked closely with my customers and they always spoke highly of our web site and the customer extranet. Tim's knowledge of rich media technologies is unrivaled."

Alex Barajas, Sales Engineer at Neustar

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