Most famously, Cutler was a founding investor in metasearch website Kayak in 2004.
That early confidence paid off when General Catalyst Partners — the VC firm he co-founded in 2000 — earned $460 million in Kayak’s 2012 IPO and subsequent acquisition by Priceline Group.
Other profitable investments by the managing director of General Catalyst include airline ticketing technology platform ITA Software, which was sold to Google for $700 million in 2011.