Sam Shank, serial entrepreneur and travel industry vet, set out to make an app-only business that appealed to the spontaneous traveler with Hotel Tonight in 2010. That was a time when relying solely on a mobile-device audience was a novel idea. An easy-to-use interface allows travelers to book their stays the day of arrival (and up to seven days in advance). The company sells unsold rooms at boutique and independent hotels and capitalizes on the millennial prioritization of experience over material possession. Hear Shank talk about what inspired the idea, how he built up the app – and why the company that tried to outsmart Hotel Tonight failed to do so.