It started on a business trip. Stash founder and CEO Jeff Low was in Manhattan and loving the independent hotel experience at Affinia 50: “My room had a painting of a poem written on a chalkboard—it was obviously chosen by someone with a passion for art. People got together in the evenings for wine or to hang out by the fire. It was like being part of a very cool club or having your own New York City apartment—with housekeeping.”

A loyalty veteran, Jeff wondered why he couldn’t get points for free nights at hotels like Affinia 50 across the U.S. He asked John Moser, an executive at Denihan Group. John’s answer was, “No one’s done it yet.”

What followed was a wild, Diet Coke and M&M-fuelled 10-month road trip. We took train trips to Ithaca to get advice from academic hotel sages. We lurked, as inconspicuously as possible, in airport lounges, striking up conversations with business travelers. “What would you want to see in a loyalty program? What makes your life easier on the road? Where would you want to cash in your points for that dream vacation?” Hours and hours were spent mapping and remapping the business plan on sheets of paper spread out on beds and bartops of hotels all over the country.

Not just any hotels.  A French colonial manor overlooking Charleston Harbor. West Hollywood villas with subterranean tunnels so celebrities can come and go in private. An oceanfront Florida resort designed by David Rockwell with a powdered-sugar beach. These hotels—French Quarter Inn, Sunset Marquis, The Portofino Hotel & Marina—and about 60 others became the first wave of Stash Hotel Rewards in 2010.

We still hang out in airport lounges and ask travelers what they’d like to see us do better. We still eat too much candy. And the private apartment-like rooms at Affinia 50? They now come with a very cool perk along with the original art: points for free nights.