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 costs, restoring customer focus—and why promoting from within beats chasing outside stars. He also w...
Apr 14, 2025•2 hr 44 min•Ep. 238
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,” why he moved to a single-CEO model, and how tough structural changes set the stage for leaner, fast...
Apr 07, 2025•2 hr 35 min•Ep. 237
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 why 50% of the Fortune 500 trusts Zscaler, why he still interviews candidates, and how he’s incubating...
Mar 31, 2025•57 min•Ep. 236
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 all in.” The mission of powering “more effective and accountable government” has been stable since ...
Mar 24, 2025•1 hr 16 min•Ep. 235
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 it took 6 to 12 months before he stopped checking his email, social media, and calendar with the same...
Mar 17, 2025•1 hr 11 min•Ep. 234
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 shoppers. But eventually, Blake found the courage to be more audacious and do something closer to h...
Mar 10, 2025•1 hr 29 min•Ep. 233
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 officer,” George says, referring to his previous role. “There's also a lot more external commitment ... I...
Mar 03, 2025•58 min•Ep. 232
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 clear: Silicon Valley cannot and should not try to disrupt the legal profession by automating the job o...
Feb 24, 2025•1 hr 6 min•Ep. 231
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 to Helsinki every winter. “You could argue that Slush was my university for things leading up to Wol...
Feb 17, 2025•1 hr 22 min•Ep. 230
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. A couple calls later, he reached ByteDance founder and CEO Zhang Yiming, who said he’d rather sell t...
Feb 10, 2025•2 hr 52 min•Ep. 229
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” as the high-pressure world of a Michelin-starred restaurant in Chicago. But he’s started working w...
Feb 03, 2025•1 hr 20 min•Ep. 228
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 100 to 1, any finance person will tell you, you should take that bet all day long.” One of those bets ...
Jan 27, 2025•1 hr 16 min•Ep. 227
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, the executive team took an unusual step: They went on the offensive, publicly calling BS on the agen...
Jan 20, 2025•1 hr•Ep. 226
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 deciding to stop and go a different direction. As agentic AI becomes more common, the people building compa...
Jan 13, 2025•1 hr 12 min•Ep. 225
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 it’s impossible to find a creative or productive flow inside of mainstream work culture. Open offices...
Jan 06, 2025•2 hr 34 min•Ep. 224
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 fire (29:41) - John Hanke on intensity and balance (38:00) - Rony Abovitz on whether losing he's bitt...
Dec 30, 2024•1 hr 5 min•Ep. 223
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 success of Candlestick Park’s replacement, Oracle Park, Baer — now the CEO of the Giants — embarked on...
Dec 23, 2024•1 hr 11 min•Ep. 222
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 right time a lot of times.” That said, he also encourages his children to proactively be curious, so...
Dec 16, 2024•1 hr 9 min•Ep. 221
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 plant, whoever is your God ... they can’t violate physical laws. How well would they do?’ And then ...
Dec 09, 2024•1 hr 15 min•Ep. 220
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 write a thing called an operations order ... [and] one of the most important things at the operations...
Dec 02, 2024•1 hr 5 min•Ep. 219
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” — but decided to say yes out of a sense of duty to Etsy’s users and workers. “If I can be helpful, I...
Nov 25, 2024•1 hr 10 min•Ep. 218
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’s incumbent on any new startup to hire in the San Francisco Bay Area, because of how exceptional ta...
Nov 18, 2024•1 hr 1 min•Ep. 217
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 is backed up by the data: Personalized tutors — designed to help students achieve mastery in a subject...
Nov 11, 2024•47 min•Ep. 216
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 being a hobbyist airplane pilot, who can’t get a license without knowing all the minute details about t...
Nov 04, 2024•1 hr 5 min•Ep. 215
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 Seattle visited his business school classroom. Most of Jason’s classmates predicted the failure of this s...
Oct 28, 2024•2 hr 30 min•Ep. 214
Guests : Joe Thomas, CEO and co-founder of Loom; and Ilya Fushman, partner at Kleiner Perkins Loom CEO Joe Thomas had a lot of things to think about before he sold his company to Atlassian for $975 million: The impact an acquisition might have on the product, how to keep the Loom brand alive, the risk of remaining independent... but it wasn’t until after the deal was announced that he really understood what it meant for his team. “I didn't know how emotional it'd be for me,” Joe says. “All of th...
Oct 21, 2024•57 min•Ep. 213
Guest : Rony Abovitz, founder & CEO of SynthBee SynthBee CEO Rony Abovitz grew up “really believing” in Star Wars and the idea that there could be benevolent, artificially intelligent beings like R2-D2 and C-3PO. “It wasn't a dystopian vision of the future,” he says. “It wasn't HAL from 2001. It wasn't the Terminator. It wasn't Skynet. It was this kind of friendly, empathetic, more utopian vision.” George Lucas himself told Rony to tone it down and not “take it so literally” — but he was und...
Oct 14, 2024•2 hr 34 min•Ep. 212
Guest : Sebastian Siemiatkowski, CEO and co-founder of Klarna Living and working in Stockholm, Klarna CEO Sebastian Siemiatkowski thinks a lot about how he’s perceived in Silicon Valley: “I feel like here I am, I am the small, country cousin from Sweden.” And on top of that, he knew that someone like Sam Altman wouldn’t initially think of a European banking startup as an ideal partner for OpenAI — so, he made up an excuse to fly to San Francisco and meet with Altman. “I felt like, OK, this is go...
Oct 07, 2024•1 hr 9 min•Ep. 211
Guest : Kyle Hanslovan, CEO & co-founder of Huntress; and Ev Randle, partner at Kleiner Perkins Talk is cheap, says Huntress CEO Kyle Hanslovan: “I learned real early on that integrity is like one of the very few things, if not the only thing, you can't buy.” En route to Huntress’ current status as a $1.5 billion firm with $100 million in ARR, he took a long time to hire new execs, or partner with VC firms. Indeed, Kleiner Perkins partner Ev Randle recalls the deliberation Hanslovan underwen...
Sep 30, 2024•1 hr 8 min•Ep. 210
Guest : Mark Fields, former president & CEO of Ford Motor Company and chairperson at Planview In 2005, Mark Fields was asked to run the Americas for the Ford Motor Company, a role he would serve in for 7 years, later becoming COO and then CEO. His wife and kids were used to relocating for Mark’s job, but had just put down roots in Florida. He told them that this time, they should stay put — he would commute between Florida and Detroit every week, and call home for an hour every night. “I pro...
Sep 23, 2024•1 hr 15 min•Ep. 209
