To take the "suckage" out of planning trips Adam Goldstein and Reddit cofounder Steve Huffman created Hipmunk, a combination airline ticket search service and aggregator. Instead of the staid old Orbitz approach, Hipmunk lists flights in a timeline, collected on one long page, and sorted by schedule, price, and "agony"--a combination of the number of stops/duration and price (although not the relative hostility of the flight attendants onboard, unfortunately). Soon after launching in 2010, however, they found that airlines were cutting commissions, so they pivoted to hotels--you can search based on price, quality, distance, and "ecstasy," a combination of price, reviews, and amenities. They'll even throw in Airbnb results--as you'll see in the video below.
What's a Hipmunk? Goldstein searched far and wide for a company name that would be a.) memorable and b.) available as a domain. He even went so far as to register BouncePounce.com and Trot.me. Finally, his girlfriend suggested he think of a cute mammal to base his brand on, and Hipmunk was born.