If you're the kind of person who generates content and by content I mean the video or audio or written materials, you're now actually going to think of how can you repurpose the content you create; that way you do the work once, but it can be used in many different ways.
Along that same line of thought, can you take the webinar recordings you take and turn them into articles? This is a difficult question because on a webinar you might be talking for one hour or longer. You might have a lot of introductory text that does not really apply to an article. You might be answering individual questions that don't make a lot of sense when transcribed or used as an article. What do you do instead?
What I would do instead is dictate new articles. I would think about what points I hit on during the webinar; what questions I answered and use each of these points and each of these questions as individual articles. I would write them from scratch or dictate them and I get them transcribed.
If you have some kind of a community which means you're running a live class with a lot of devoted students, see if your students can post their notes in the members' area. What I do is I have a blog where I post the webinar recordings and I tell people, "If you took notes during the webinar, leave them as comments here so that everyone can use them." Then what you do is you take that outline and use it to create new articles. You after all are the best person, the most qualified to write these new articles because these notes are based on things you talked about.
I have tried giving videos to outsourcers to have them create articles but many of them don't get the point. There's nothing wrong with that. They simply you have don't have the same area of expertise as me; they're not trained with the same niche so they don't understand the point I was trying to make and the articles don't sound like me. On the other hand, if I dictate articles and they are transcribed, the articles are written in my exact voice.
And finally, if you're thinking about getting the entire hour or two of the webinar transcribed and then edit it into individual articles, it's a waste of money for the reasons I stated above. When you transcribe an entire webinar, you're also transcribing all of the chitchat, the introductory information and the question-and-answer session when it would be easier and faster and better for you to look at what points you touched on and create new articles from scratch.
You shouldn't spin your webinar recordings directly into articles but you should spin the ideas in the articles. Dictate or use the student notes as your outline; don't trust outsourcers to write their own articles and don't transcribe the entire webinar. Take the ideas you had; make them into your own brand new articles.
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