I can support Fast Bob, and say this is in fact possible. My progression:
2005 Flight Instructor $18,000 USD
2006 Flight Instructor $24,000 USD
2007 Air Cargo piston twin - turboprop - Falcon 20 $28,000 USD
2008 King Air in ME $115,000 USD
2009 Falcon 2000 in ME $84,000 USD
2010 King Air 350 in ME Housing, Car, Insurance and $108,000 USD
plus soon a Lear 60 XR upgrade.