Potential Rollup (Not sure if there is a bigger play here or not)

I am in Chicago and I run a few lead Companies. I work closely with 4-5 other Companies and we have been talking about potentially doing some sort of rollup (maybe IPO). Top line is 100M+ right now (between 2-3 of us), and expected to grow from there. (Mainly in the Insurance and Debt space)

Not sure where to start with this so I figured I'd post in here to see if anyone had any experience taking already existing Companies that generate a lot of Cashflow and rolling it up into a much larger play.

This is COMPLETELY out of my World, but I figured People in here may be able to point me in the right direction, or tell me I'm insane for even considering it. Idk - I figured it's worth a shot to ask to see if there is a much larger play to be made here than just cash flowing these Companies year in year out.