Prerna Gupta, co-founder of storytelling platform Hooked, shares a tough lesson she learned from her mentor, and what she does now to pay that lesson forward. --As told to Nick Hawkins
Ron Conway is basically the godfather of Silicon Valley. He was an early investor in Google, Square, and Airbnb.
But when I met him at a party in San Francisco in 2017, I was filled with self-doubt. Our storytelling app, Hooked, was in its second year, and one of our seed investors had expressed interest in leading our Series A. But then he turned around and led the Series A for a company that had cloned our app.
My husband--who's also my co-founder--and I were pretty upset, and a lot of our investors were like, "This is really messed up. You need to kick him off the cap table. You need to tell him, and other people, that he's a jerk." I was sharing all of this with Ron, and told him I was worried I was too nice to be successful and needed to learn how to be a jerk.
Ron said, "Nice people win bigger in the end." He told me that you can be aggressive in business but still be kind to people. He pointed to examples like Airbnb's Brian Chesky, and told me I could stand up for myself without burning bridges, that it was better to treat everyone with compassion--and to keep in mind that my relationship with this investor might prove useful later on.