Grit

Amplitude helped define the modern analytics stack, powering digital products with deep behavioral insights. But in a world shifting toward agentic interfaces and vertically integrated AI, even a category leader has to evolve. In this episode, CEO Spenser Skates shares how he’s rethinking AI within the constraints of a

Flexport was a breakout success—reimagining global trade with tech at its core. But when the freight market cooled and efficiency overtook service, things started to unravel. Founder Ryan Petersen stepped aside, handing the CEO role to former Amazon exec Dave Clark. Months later, he was back at the helm. In this episod

Guest: Pedro Franceschi Pedro Franceschi is the co-founder and CEO of Brex, a fintech company reshaping how businesses manage their finances. Originally from Brazil, Pedro went from teenage hacker to leading one of the most well-known names in modern financial technology—building a platform trusted by startups and ente

Before Zscaler was a $32B cloud security giant, it was just 10 engineers—half in Bangalore, half in a borrowed U.S. office. As founder and CEO of Zscaler, Jay Chaudhry bet $50M of his own money on one radical idea: secure the internet in the cloud. Born in a Himalayan village with no electricity, he built Zscaler into

Guest: Zac Bookman, CEO and Co-Founder of OpenGov Thirteen years after co-founding the government transparency startup OpenGov, Zac Bookman is still finding ways to surprise people. In 2024, Cox Enterprises bought the company for $1.8 billion — but as far as Zac is concerned, “we’re just getting started.” “ I left the

Guest: Ben Chestnut, Former CEO and Co-Founder of Mailchimp If you find yourself selling your startup, then Mailchimp co-founder Ben Chestnut has some important advice for you: Get a dog.  When Intuit bought Mailchimp in 2021 for $12 billion, the company asked Ben if he wanted to stay on as CEO, but he chose to “walk o