In May of 2010 I was working at a subsidiary of Silicon Valley Bank (SVB), where I spent all day talking to smart people—CEOs and founders of disruptive companies seeking to achieve the impossible. This gave my team a unique window into products, companies, and brands that didn’t exist yet—but probably would someday. One afternoon Christian Groh (my SVB colleague and longtime friend) and I met with a California start-up that described itself as a “medical-cannabis technology company.” We didn’t like the company’s team, strategy, or business model, but the much bigger issue was that we didn’t know how to evaluate a start-up in that space, because we’d never thought about cannabis as a legitimate business opportunity.

A version of this article appeared in the March–April 2020 issue of Harvard Business Review.