Dave, TeachStreet’s CEO, has a guest post up on TechCrunch today about our transition from a free to a paid service.

Dave calls out the following five tips to make the transition go smoothly:

  1. Give your customers plenty of notice, and give them a (real) chance to comment/contribute feedback.
  2. Price it ‘fairly’ (probably still at a deep discount)
  3. Offer your customers a way to get your product for free
  4. Provide Grandfather’d Pricing for long-time customers, or give them exclusive benefits
  5. Make the transition gradual, if possible — people should only pay if you’re delivering value

He also shares a bunch of details about TeachStreet’s history and evolution - a.k.a. the story of my life. We’ve still got a long ways to go, and certainly don’t have everything figured out yet, but hopefully you can take something away from the article and our experience.