A))) First, spend a good deal of time thinking up a great product or course to give away free. A good way to do this is look at products that are for sale in a niche, and figure out how you can give away something similar for free.
For example, if you see someone is selling a product on "Facebook Advertising" see if you can create a cool product (a sacrificial lamb) to give away free. Treat it like it's for sale, even though it's free. Make it very valuable.
B))) Create a squeeze page that gives that thing away free... where people have to opt in to get your free product.
C))) Set up a OTO offer. Right after they opt in to get your free product, the next page is a OTO that pitches an offer. Say on your OTO the following, "Your free course will be sent to you in just a minute, but while I have you, we are running a special test. Watch the video below and this is the only time you'll ever see this video. If you click away it could be gone forever. On that video (or copy) sell them on a special, special one time offer.
D))) Drive traffic to your squeeze page.
E))) Tweak, test, measure and track.
F))) Continue to give free tips and insights away to your subscribers, but also mix in offers of your own or affiliate offers.
G))) Continue focusing on this system you have. Continue to focus 90% of your time on traffic and conversions. Everything else that takes up your time would be a distraction, or education.
Your biggest question right now (If I had to guess) would be... how do I get that traffic?
Good question, but there should be another question and that's "how am I going to convert that traffic?". If you can convert well, then traffic is an after thought. You'll see what I mean if you actually get off your butt and drive traffic. However, here's how you generate traffic:
1))) You pick one way to generate traffic and you stick to it, master it and become the best at it.
2))) Pick if you are going to focus on free traffic or paid traffic.
3))) For free traffic, my recommended technique is JV Affiliates. Set up that OTO with an affiliate program and go out there and recruit affiliates. It takes having leverage to get them. Spend a great deal of time coming up with your plan to get JV Affiliates to agree and promote your stuff.
Since everyone here is into Article Marketing, go ask an Article Marketer pro here how to do it or buy their products. I dont recommend it myself, but it does work. Up to you.
SEO/BLOG/Articles/Linking/web 2.0/etc all works, but I recommend none of it for traffic myself.
I recommend: JV Affiliates or Paid traffic.
4))) Paid traffic. Ok, Imagine paying $4,000 to get a list of 5,000+ If you knew for certain if you spent $4,000 you'd get a list of 5,000+ would you spend it??
A list of 5,000+ managed correctly could generate $60k+ per year. Imagine spending $4000 and make 60k per year for the next 3-5 years. Would you spend it?
All in all, it comes down to how you are going to generate subscribers. I bet there are plenty of people here who have a list like that just from running WSO's. BUT, do you manage that list right? Because, there's 60k per year sitting there in your autoresponder account.
So, Dude... where's your list?