Having done this experiment with a few variations over the years, maybe a dozen times, I've found that the first $100 is the roughest.
I'm currently in one now with a buddy and we're going for a grand sum. Exciting. But, we started with $20 each in the pot.
When I was in college, I had two concurrent experiments running. Player one was only allowed ethical & legal investments. Player two, well, basically did whatever. Player two crushed player one. It was the 80s. Each player started the contest with one penny. Player one ended up with about $80 in 60 days. Player two was something like $1200+.
I promise to plug it here when its done, but we're documenting this game and also publishing a pamphlet / ebook on the basics of playing. Like I said, there are some real challenges getting past the first few dollars. Depending on your rules of course.
It's all good fun, if it is for fun. But it's also good to remember while playing a money race, the times when you were flat broke. And if you never had that challenge, try to imagine people who deal with the struggle to eat and shelter every night. Of course, this is another version of the game - Walking Out. Take only what your seed for the game is (one cent, $100) and walk out of the house. Good luck!