StayDreamer and the SXSW ‘shakedown cruise’

When StayDreamer launched at SXSW this year, “it went through a shakedown cruise.”
That’s how founder and CEO John K. Hart viewed the opinions of festival goers, who got a sneak peak of the integrated hotel ogling and booking app at a TechBreakfast event in Austin.
“South By brings together a really interesting mix of people,” he said. All the more to test out and critique the app— and understand for one that its Pinterest-integrated model appealed more to women than men. “It was very anthropological,” said Hart.
StayDreamer lets users make simple hotel reservations, but it draws them in by allowing them to create lists of their favorite locales and follow expert reviewers from other websites like TrustYou.
The platform is the third customer-facing product designed by Imagine If, a company founded in late 2013 by two former Marriott executives, Hart and Humberto Chacon, along with CTO Tim Kosmider and EVP of product development Andy Stewart.
Based in Arlington, the company now has seven full-time employees and is in the process of raising a $1 million Series A round, after a $3 million seed round announced last November.
For Hart, competitiveness between the hotel industry and online travel agency websites is a waste.
“It’s a big market and it has a lot of pain points,” said Hart. “Hotel companies and online booking companies, they won’t admit it but it’s like war.”
With Imagine If, he hopes to create online booking products that benefit hotel chains, while entertaining a more sustainable business model.
Just as Best Buy became “a showroom for Amazon,” he said, “all the frequent travelers are showrooming” with Priceline, Expedia and other travel agencies. Then, they go to the hotel websites to make their purchases.
To avoid that, Imagine If has honed in on that very population. “We give them the rewards, we give them the same relationships and we give them the hotels,” he said.