When its time to monetize

[theBiz]

I am wondering how to approach this situation. I will be giving out a free service i already have pre free signups. I will be giving the service for free then when i feel it is time (6mo-10mo most likely) i want to send out an email saying hope this was of value to you, if you would like to continue please sign up here for X/month. I remember MJ saying he did something along the lines of this but this is a monthly service. What should i do to test the market before i do this?
I do not want to charge $10 per month to the existing free customers when i could really get $90. I also would not want to get 100 people at $10 when i could of got 50 people at $90. I have never done this before but figured everything out step by step to get to this stage. The problem is this is go time, make money or not, no mistakes can be made here because you cant tell them $10 bucks then re offer it at $90 when you realize you can get more. Also, you do not want to offer the service at $90 then get no one so you reoffer it at $10. These are not actual numbers just examples. If anyone has dealt with this or knows about this step please inform me, thank you.

Also i have looked at competition but there is no way to figure paying people % so it does not help me too much.

 

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[Rem]

Example:

" On September 1st we will be charging $90 for new sign-ups. The first 1,000 members will receive a discount for the next 2 years at $10. Make sure to sign up now before the regular price of $90 kicks in. "

This allows people to see the value ($90) and then see the savings at $10.

By just charging $10 all people will see is themselves being charged money. They need to see the value and some sort of deal.

Good luck and let us know how it goes.

 

[theBiz]

Great idea remdog, so they will see the value in the product first (first few months they had free) then show them its going to be more money later, make them feel as if they are getting a discount. At this time when i send out the email i am putting a call to action at the bottom though correct? On sept 1st we will be charging $90 per month for a membership, the first 1000 members will receive a discount membership of $10 per month, sign up now to receive your discounted package. something like that?

Also any tips on the entire process. How to label the email heading, and lead them directly into a paying sign up page? I was thinking leading them into a 2 step page. 1st page is like a "what you get page" then they click next then it leads them to blank entries CC info ans such.

What gets the best results i have worked a long time to get here i want to do it right haha.