Grit

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 episode, Ryan explains what went wrong, how he’s rebuilding Flexport—cutting $300M in...

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 enterprises alike. In this episode, Pedro shares what it took to launch “Brex 3.0,”...

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 one of the world’s top cybersecurity giants. In this episode, Jay breaks down wh...

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 vast majority of my net worth in the company,” he says. “So I'm a believer. I'm...

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 off into the sunset” and let the new owners take over.  After that, he estimates...

Guest : Blake Scholl, Founder & CEO of Boom Supersonic “Passion and drive trumps knowledge and experience,” says Boom Supersonic CEO Blake Scholl. Long before he was running Boom — which earlier this year successfully tested the world’s first privately-developed supersonic jet — he was enabling “the world’s most obnoxious spam cannon” at Groupon, or designing a barcode-scanning game for retail...

Guest : George Kurian, CEO of NetApp For almost 10 years, George Kurian has been CEO of the data infrastructure firm NetApp, overseeing its pivot to cloud services. After he  took the job — a surprise promotion dropped on him just days before it was announced — he had to learn on the job how the job could be. “ There are a lot more stakeholders that a CEO has to deal with than a chief product offi...

Guests : Winston Weinberg, CEO & co-founder of Harvey; and Ilya Fushman, partner at Kleiner Perkins “If you think about pretty much any job out there in the world, we will have some sort of [AI] copilot,” says Kleiner Perkins partner Ilya Fushman. “The question is, who are the right folks to build it, and what’s their vision?” For Harvey CEO & co-founder Winston Weinberg, the vision is cle...

Guest : Miki Kuusi, head of international at Doordash + CEO & co-founder of Wolt + co-founder of Slush tech conference Before Miki Kuusi launched the Finnish delivery startup Wolt, which DoorDash acquired in 2022, he wasn’t just another startup entrepreneur. From 2011 to 2015, Miki was the CEO of the hugely influential European tech conference Slush, which brings thousands of founders and VCs...

Guest : Bobby Kotick, former CEO of Activision Blizzard; and Bing Gordon, Advisor at Kleiner Perkins In 2020, when President Trump signed the executive order that would ban TikTok in the U.S., Bobby Kotick called his old friend Steven Mnuchin. The former Secretary of the Treasury told him that, if TikTok’s U.S. operations were to be sold to an American company, Microsoft would be the only bidder....

Guest : Nick Kokonas, co-founder of the Alinea Group and former CEO of Tock As of October 1, 2024, Nick Kokonas is no longer an owner of the Alinea restaurant group, which he co-founded and ran for almost 20 years. When he bought a vineyard in Napa Valley prior to the exit, one of his sons remarked, “He's given up. Time to go out to pasture.” Nick admits that the work ahead of him is “not the same...

Guest : Rick Smith, CEO & Founder of Axon (formerly TASER) Being a founder-CEO is a “unique superpower,” says Axon’s Rick Smith: People like him get a longer leash from the board to try things that outside CEOs might not. “My job is to push risk into the organization,” Rick says. “If there's a project with a 50 percent chance of success, a 50 percent chance of failure, but it's going to pay 10...

Guest : Emilie Choi, president & COO of Coinbase After the collapse of FTX in 2022, “the whole industry was tarnished,” recalls Coinbase COO Emilie Choi. “Politicians came out criticizing crypto, saying it was a fraud.” But unlike FTX, Coinbase was a public company in the U.S. So when the SEC served it a Wells notice, announcing its intent to charge the company with violating securities laws,...

Guest : Sarah Franklin, CEO of Lattice As the CEO of a growing company, Lattice’s Sarah Franklin has learned that one of her most important contributions is taking a leap of faith. “You have to have the courage to be the first one to do it,” she says,” and to show that it can be done, and to pave the way so that then your team feels trust.” Sarah cautions, though, that sometimes courage is decidin...

Guest : David Heinemeier Hansson, CTO & co-owner of 37signals and creator of Ruby on Rails  37signals CTO David Heinemeier Hansson has organized his life around his passions: Writing, racing sports cars, and coding. “ Why aren't we all doing that?” he wonders. “Why aren't we all trying to optimize our life in such a way that much of it is enjoyable?” Part of the problem, David argues, is that...

On this special episode of Grit, we look back at some of the coolest stories and best advice our guests have shared in 2024. Chapters: (00:49) - David Risher on his Amazon easter egg & moving on (07:02) - Jason Kilar on bouncing between relevance & irrelevance (15:13) - Eoghan McCabe on "re-founding" the company he started (22:59) - Mark Fields on battling with Trump & running to the f...

Guest : Larry Baer, CEO of the San Francisco Giants In 1992, Larry Baer was part of the ownership group that bought the San Francisco Giants and successfully prevented the team from being moved to Tampa, Florida. Back then, they had a big problem to solve: An old, uncomfortable ballpark that voters wanted to see replaced, but didn’t want to pay for. 20 years after the construction and financial su...

Guest : Tony Vinciquerra, outgoing CEO of Sony Pictures Tony Vinciquerra never planned to get into the entertainment business, let alone to become one of the most powerful people in Hollywood. After seven years, he’s about to leave the CEO role at Sony Pictures (although he will stay on as chairman for one more year) and attributes much of his success to luck: “I’ve been in the right place at the...

Guest : Jeff Wilke, former CEO of Amazon Worldwide Consumer and chairman of Re:Build Manufacturing Jeff Wilke worked more than 20 years at Amazon, overseeing the million-person team that speedily gets packages from warehouses to doorsteps. In hindsight, he observes that Amazon Prime’s exponential growth was actually an incremental daily process. “I used to say things like, ‘If God was running this...

Guest : Dan Streetman, CEO of Tanium A graduate of West Point who served in Iraq combat operations, Tanium CEO Dan Streetman can’t help but compare his business career to his military experience. Understanding huge structures and processes is a crucial skill at both Tanium and in the Army, he says, as are the skills for aligning people around a shared mission. “Before you go on an operation, you w...

Guest : Josh Silverman, CEO of Etsy When Josh Silverman joined the board of Etsy, he had one condition: “Don’t ask me to the be the CEO.” And technically, they didn’t ask. One day, he got a phone call informing him the board had elected him as the new CEO, just days before an earnings miss. He knew the odds were against him — layoffs would be necessary, and “I was going to have to be the villain”...

Guests : Varun Mohan, CEO & Co-Founder of Codeium; and Leigh Marie Braswell, partner at Kleiner Perkins “A lot of people are really bad at knowing what good is,” says Codeium CEO Varun Mohan. Specifically, he’s thinking of startups that hire based on a “logo” — a well-known company on the résumé — rather than exceptional talent. Codeium is based in Mountain View, CA, and Varun believes that it...

Guest : Sal Khan, founder of Khan Academy AI is poised to change nearly every business, but few are changing as quickly as education. And Sal Khan, who has spend more than a decade manually creating more than 7,000 educational videos, says that’s a good thing. He’s encouraged Khan Academy to focus on “disrupt[ing] ourselves ... more than almost any other organization that I know of.”  The reason i...

Guest : Matt MacInnis, COO of Rippling One of the most important things a non-founder can do, says Rippling COO Matt MacInnis, is to learn how to operate in the context of the company they’re joining. His CEO, Parker Conrad, “spikes” in certain skill areas, and the rest of the executive team needs to maximize his ability to thrive while “taking care of the rest of it.” Matt likened the work to bei...

Guest : Jason Kilar, former CEO & co-founder of Hulu and former CEO of WarnerMedia When Jason Kilar was a child, he was obsessed with Walt Disney — not just as a filmmaker or the creator of Disneyland, but as an entrepreneur. He started his career at the Walt Disney Company (where else?) but then got his first opportunity to help build something new when a young startup entrepreneur from Seatt...