Great analysis from Leon Chism on why there is no “Orbitz mafia” (Google “Paypal mafia” to understand that term). Simply put, the early employees didn’t make the kind of money from the initial Orbitz IPO and subsequent sale transactions to create this type of reinvestment cycle in Chicago. Orbitz was never a startup, it was a heavily backed (100M) investment on behalf of the airlines and such the airlines took the returns.

Here’s to wishful thinking that the Groupon transaction (assuming it happens) will create hundreds of new future startups within Chicago and beyond.