In this episode of the Something Ventured podcast, I talk with Sam Shank, the founder of HotelTonight—the groundbreaking last-minute hotel booking app that was acquired by Airbnb in a deal reportedly valued at nearly half a billion dollars.
Sam takes us on an incredible journey: from his early days in Hollywood as a production assistant on Wes Craven’s iconic horror film Scream (yes, he has an IMDb credit!), to pivoting to tech during the dot-com boom, surviving the crash, and founding multiple startups in the brutal travel space. After two tough swings that taught him invaluable lessons about product-market fit, distribution, and avoiding incremental ideas, Sam spotted a massive opportunity in mobile same-day hotel bookings.
Sam shares how HotelTonight cracked the App Store rankings, turned perishable hotel inventory into gold, and ultimately became a perfect strategic fit for Airbnb. Now, Sam is back at it with his new venture in wildfire insurance—using cutting-edge science and AI to make high-risk homes insurable and literally save lives.
We also dive into Sam’s reflections on Silicon Valley’s evolution, the future of AI in travel distribution, self-driving cars, and why building things still excites him after all these years. Hopefully you’ll find it a candid, inspiring conversation with a resilient founder who proves that great outcomes often come on the third try.
Timestamps
00:00 – Intro & How Kent Met Sam
03:29 – From Hollywood (Scream) to Silicon Valley
09:41 – Early Startups & Lessons from Failure
19:35 – The HotelTonight Origin Story
27:18 – The Airbnb Acquisition
29:52 – New Venture: Wildfire Insurance with Science & AI
38:48 – Silicon Valley Then vs. Now + AI’s Impact