Given you have a good idea of where to start and are fairly confident you are speaking the same language as your client, jump start research by generating related keyphrases and long tail variants with the ever so easy to use Google Autocomplete. This tool makes predictions based on what you are typing that are a reflection of Google search activity.
"With Google giving over the home page to ads and their own properties for commercial keywords, the Long Tail keyword is more important than ever. If you have a website, you know that most of your traffic comes from keywords you never would have thought of. With Keyword Researcher, you can find them in advance and make sure that you're the one that snags this traffic. I use it for all of my e-commerce site planning."
A very popular and highly competitive keyword on Google search engine is "making money." It has 85,300,000 search results, meaning that millions of websites are relevant or competing for that keyword. Keyword research starts with finding all possible word combinations that are relevant to the "making money" keyword. For example, a keyword "acquiring money" has significantly fewer search results, only 61 000 000, but it has the same meaning as "making money." Another way is to be more specific about a keyword by adding additional filters. Keyword "making money online from home in Canada" is less competitive on a global scale and therefore easier to rank for. Furthermore, keywords also have various intents which can affect whether the marketer would want to target that keyword. Multiple tools are available (both free and commercial) to find keywords and analyze them.

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Because great content requires a deep understanding of the main idea (e.g., “ac repair houston”) and the supporting subtopics that require coverage (e.g., “central ac vs portable ac systems”) and the common issues that users seek answers for (e.g., “freon,” “refrigeration loops,” “coolant refills,” “troubleshooting”), the effectiveness of a keyword reporting tool is only as strong as the SEO pro using it.

3) Google: This is pretty straight forward but it’s the main reason I like it. I search for my main seed keyword in Google, and use the keywords that Google itself highlights in bold on the search results, plus the “Searches related to” section at the bottom to get keyword variations or LSI. That’s basically what Google is telling you that topic is about. No need for a thousands other tools. I use these to optimize the on page of my target pages as well.
Trying to rank for the keyword “Best Headphones” will see your post, page, or article buried in the depths of a billion search engine pages, and it’s never going to surface in the top thousand pages, let alone page one…ever! But going for a keyword, or Long Tail keyword phrase “What are the Best Headphones for Sleeping” will stand you in better shape to get somewhere close, or even on, the first page.
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Within a matter of seconds, Long Tail Pro showed me the top 25 Adwords suggestions for my seed keyword, with KC Scores already calculated! After scanning the list, I found a couple of keyword ideas that I wanted to drill further into. One of these was the keyword – legitimate work from home jobs. This keyword by itself would be very difficult to rank for (KC Score of 40) – but the new cloud version of Long Tail Pro allows me to easily grab up to 20 more suggestions based just on this keyword. I clicked the button to do that (as shown in the image below).

The Google Keyword Planner used to be great it's now frustrating to use.... and almost impossible to get in to without setting up your first ad. Big shame google big shame. I would love to share more info about your tool over on my website [link removed by moderator] for my local business clients - have you got something you can send over for me to add to the site?
I want to share how and why I sold the company in order to both educate and inspire potential software entrepreneurs.  I certainly don't know everything and obviously companies sell for much more than I sold Long Tail Pro for (I won't be featured in Tech Crunch anytime soon); however, I'm willing to share what I have learned and hopefully that can be beneficial to a few of you.
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