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 costs, restoring customer f...

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 sin...

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 trus...

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 power...

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...

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, Bl...

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 ...

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...

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.

 “Y...

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 reac...

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 ...

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 wi...

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 un...

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 ...

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 cre...

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 ...

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 r...

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.” 

...

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 ....