I don't have experience with ad-based to paid, but going from beta and free with 100k users to paid in a market with a lot of competitors has been interesting,

I don't have experience with ad-based to paid, but going from beta and free with 100k users to paid in a market with a lot of competitors has been interesting, in a good way. I think though it depends who is going to be your customer. If they are businesses, many of them prefer to pay as it's normal to them and they can expect certain things when they pay for something. Once the first bit of paid revenue came in I forgot about all my fears of alienating the customer base and driving them to competitors. Users that expect things to be free tend to be fickle anyways. For consumers, I don't know, but more of them pay than you'd think.