Hotel Tonight Co-Founder (and SCH Parent!) Shares 10 Lessons on Thriving in a Crowded Market

Last week, as part of the CEL’s Founder and Leaders Series, Jared Simon P'37, co-founder of Hotel Tonight, a last-minute hotel booking site, distilled the company’s decade-long journey—which culminated in an acquisition by Airbnb in 2019—into 10 practical lessons on “finding opportunity in a crowded market.” Simon joins other accomplished SCH parents who have shared their entrepreneurial experiences with students.

Among his practical tips was simply to “knock it out of the park.” Hotel Tonight succeeded by seizing the mobile platform shift, he said, delivering an experience so superior that it compelled customers to switch. One revolutionary idea? The 3-tap, 10-second booking process. While users of other platforms were booking for a long 7 minutes and hundreds of taps, Hotel Tonight won over users and hotel partners with the simplicity of its platform. 

Simon’s counsel also centered on disciplined execution, self-reliance, and self-confidence. He stressed that success depends on sequencing, urging founders to prioritize only the single most critical question that could break the company. Above all, he emphasized self-confidence when advising founders: “Listen to all the advice, but no matter how much great experience others have, nobody is smarter about your business than you are.”

Selected students also had the opportunity to pitch their ventures, gaining valuable feedback from a successful entrepreneur.