95: HotelTonight CEO Sam Shank, Plus Cannabis Goes Legal in Canada


This week, Canada legalized pot. That’s a big deal because it’s the largest country to do it, and because it’s a major milestone in one of the most impressive rebranding exercises in a generation. When I was growing up, many warned against marijuana as a gateway drug, the province of hippies and slackers. Now it’s becoming a multi-billion-dollar global industry, and Elon Musk is toking during a podcast. Seems like an appropriate time to polish off that old meme: “We would like to congratulate drugs, for winning the War On Drugs.”

For the Fortt Knox 1-on-1 this week, I bring you my conversation with Sam Shank, cofounder and CEO of HotelTonight. That business is another example of seizing the moment. Shank had achieved smaller success with a travel technology businesses in the past, but this one was timed to a revolution when it came to life eight years ago. The idea: a smartphone app that finds you last-minute deals on hotel rooms. At first, you couldn't book any further out than a week in advance.

The concept has evolved significantly since then. Today, it’s not just on smartphones, and you can now book three months in advance. The startup has raised more than $100 million. Shank has some advice for aspiring entrepreneurs, intriguing insights into why HotelTonight needed to start the way it did, and an update on the prospects of an IPO for the company.