Interesting theory. No, I have not won the lottery.
This site and USA Mega (and some others) were founded and created by me starting in 1999 (13 years ago), opening in 2000. I created them at night, while during the day I worked as a technology consultant.
I decided to create the web sites because at the time there was very little reliable information on the Internet about lotteries. The use of technology on the sites that did exist was very poor, and much of what existed was "scammy". (Sadly, I guess not much has changed in that department.)
I had no previous knowledge how to do this kind of thing, no advice from anyone, and there was nothing out there to copy or model anything on. I basically dreamed up in my head how it should work and how people would use it.
You have to be very driven and self-motivated over a very long stretch of time to make something like this happen. Everyone has seen a multitude of web sites get started and disappear over the years. That's because most people look at sites like Lottery Post and not realize the magnatude of effort over the course of many years that goes into it. It becomes overwhelming -- unless you are expecting it and you WANT to take on the huge effort for the long stretch.
The other thing that becomes necessary is developing a thick skin to the constant barrage of negativity that comes your way. You realize that no matter how hard you try to please people, there will always be a certain group of people that basically say "you suck", or people that write nice things to you and then talk trash behind your back, or people who hate every single time you make any changes. You learn to separate "pure negativity" from actual useful negative feedback, and you learn to greatly appreciate when people take a moment from their day to share some kind words, just because the site has helped them in some way.
As someone earlier had mentioned, in 2007 I put together a brief history of Lottery Post including some screen captures showing the progress. It is available here. (You can also find it by clicking my name and then selecting "See Todd's shared favorites" in the popup menu; it is under Favorite Blog Entries.)
But that was done in 2007, and in the 5 years since that point the site has changed a great deal more -- so much that the last snapshot in that article is not very recognizable.
Technology has changed greatly since 1999, and the way people use the Internet has also changed with more people using mobile devices and tablets to browse the Web. So Lottery Post will indeed continue changing and adapting.
With regard to the initial question "Has Todd won the Lottery?": not only did I NOT win the lottery, but unfortunately since I started I have a lot less opportunity to even play the lottery. I guess that may be another reason why many who start lottery sites don't last very long. It takes so much time to do this stuff that you basically sacrifice your own ability to participate in a meaningful way.
I hope this answers the questions raised here. I very much appreciate the nice comments made by some!