[neilv]

I really appreciate your thoughts.

Question: When you say "best/fastest signal" and "prove that your product is something people are willing to pay for", are you speaking of proving to myself, like a bootstrapped small business? Or of proving to prospective investors?

Regarding the paid&free model, just thinking aloud... I suspect that the browser vendors are going to push me to use their extension store, so maybe I have to put the paid features as data/behavior on a server that the extension talks to. Or to send a paying customer an unlock code that flips a trivially-crackable switch in the free extension, but which at least helps keep honest users honest.

[jaredsohn]

I think you should look into making your extension 'private' at least at first and only grant access to people who pay for it. You need to add each user's gmail account to a list in the Chrome Webstore or associate a Google Group with it and then add peoples' emails to that list.

Maybe set up a server where people can pay and people can auth against later on to automate the payments and updating the users list.

[soasdfg]

I would say both in this case, you can make the decision if you think you need investment money or not and the number of paid users you have can be can be a valuable point of data used to help determine this.

You have the advantage of being able to start and potentially get something into the market without needing to take investor money and promise larger than life returns on the money you take. Use this time wisely to make an honest judgement of what you think this business could turn into, if it's just something that pays your rent then let it be that. If you grow like crazy and need investment money, only then pursue it.

Dealing with investors is a really big headache, so only accept money from them if you really think it will make a difference in being able to grow the business.

Yes you will almost certainly have to use one or many extension stores, you will also need to setup a secure way to handle subscriptions and give elevated access to users that pay.