How do I get started in Angel investing? I have a decent chunk of change that I would like to put toward more aggressive/risky endeavors. I’m in the midwest as well if that matters.

You'll get better returns in the market in most cases (or hell, tax-free munis).

Do you have F-you money? Otherwise, steer clear.

Wow do a lot of angel investors have the same attitude about their investments?

Or, let's talk! :)

I'd suggest joining one or more Angellist Syndicates. Get a feel for it, learn from your investment team and maybe start your own syndicate at some point.