I started wtih ffree hosting from a hosting company called hostingbranch.com I got webhosting in exchange for services from there I bought a dedicated server @ managed.com and moved over to tailormadeservers and now I reside with 6 dedicated servers from softlayer.com and 4 from fdcservers.net
Started with my own shared account somewhere, moved onto a reseller account, then to VPS and then onto a dedicated... probably could have skipped a few of those steps if I had been focused on creating and monetizing sites earlier
Started with personal fun websites on my ISP, Geocities, Xoom etc (had loads of hosting accounts as they only gave you something like 5 or 10 meg or something so needed to spread things around a bit...).
Now I use a simple paid-for shared account for about ... £5 a year (yes five!). Seems to me like a lot of services are brutally over priced; I've seen similar services as what I am getting advertised for anything up to $20-30 a month!