Grit

Before AI became a buzzword, a few true believers were already building.

Since early 2022, Mati Staniszewski and his team at ElevenLabs have been among them, working to create voices that “actually represent emotions.”

He shares with Joubin Mirzadegan how voice AI is transforming diverse fields, from delivering personalized healthcare for different age groups to amplifying creativity in filmmaking.

Guest: Mati Staniszewski, co-founder and CEO of ElevenLabs

Connect with Mati Staniszewski

​

Connect with Joubin

​

​Learn...

What’s product-market fit like when you give people the power to do what they never thought was possible?

On this rerun of Grit from April 2024, Victor Riparbelli, co-founder and CEO of Synthesia, shares how his platform gave billions a new way to create video without cameras, and explores a future where video and audio replace text as the primary way to share knowledge and content.

Guests: Victor Riparbelli, CEO and co-founder of Synthesia and Josh Coyne, Partner at Kleiner Perkins

Connect with Victor Riparbelli

X...

Make your product irresistible, and everything else will follow.

That’s the philosophy of Grant Lee, co-founder and CEO of Gamma, an AI design platform with an 'anti-PowerPoint approach', used by over 50M people.

This week on Grit, he also shares why enduring businesses aren’t one person shows, and how their deliberate hiring process shapes and strengthens company culture.

Connect with Grant Lee

Connect with Joubin

Learn more about Kleiner Perkins

Scaling a business globally comes down to leaders who align teams and drive them forward together.

Snowflake serves over 12,000 customers, and early executives Chris Degnan and Denise Persson share how they scaled the company while keeping the unlikely pairing of sales and marketing perfectly aligned through hypergrowth.

They join Joubin Mirzadegan to share insights from their new book, Make It Snow, revealing how they built Snowflake’s ‘go-to-market engine’ and fostered a customer-first culture across every function.

Guests: Chris Degnan, former CRO and advisor to the CEO at Snowflake, and Denise Persson, CMO at Sno...

What does it take to reinvent entire industries, over and over again?

This week on Grit, Sebastian Thrun, the “godfather” of self-driving cars and massive open online courses, reflects on a career pushing the boundaries of technology across mobility, education, and AI.

With Joubin Mirzadegan, he shares why he believes autonomous driving could become the biggest lifesaving technology in history, and how a wake-up call led him to found Udacity to truly democratize higher education.

Guest: Sebastian Thrun, CEO of Stealth Startup, founder of Google X and Udacity

Connect with Sebastian Thru...

What kind of founder builds a billion-dollar company around something anyone can use for free?

Matt Mullenweg, co-founder of WordPress and CEO of Automattic, joins Joubin Mirzadegan to reflect on two decades of building the platform that now powers over 43% of all websites through cycles of doubt, decline, and reinvention.

He also shares how Automattic aligns employees with its mission to democratize publishing and commerce through paid sabbaticals and remote work.

Guest: Matt Mullenweg, co-founder of WordPress and founder and CEO of Automattic

Connect with Matt Mullenweg

...

The apps and websites we use every day depend on systems most of us never see.

Jay Kreps joins Joubin Mirzadegan to share how Confluent became the ‘central nervous system’ for companies like Expedia and eBay, letting them respond to business operations instantly.

They also break down why the myth of AI-driven efficiency falls short, and why building truly transformative companies takes far longer than most people expect.
​
Guest: Jay Kreps, Co-Founder & CEO of Confluent

Connect with Jay

Connect with Joubin

...

Can a no-code giant reinvent itself in the AI-native era?

This week on Grit, Airtable CEO Howie Liu shares what it means to “refound” a company, how speed comes from tearing up old playbooks, and why conversational AI is reshaping his product—and his company.

Guest: Howie Liu, Co-Founder & CEO of Airtable

Chapters:

00:00 Intro
01:04 First startup & YC
04:06 Salesforce acqui-hire
07:31 Life-changing exit at 22
11:07 Scaling too fast, layoffs
14:04 Sparks vs. coasting growth
19:33 Two years to launch
24:04 Could AI Build It Faster?
27...

For Bill McDermott, work has never been just a job.

On this Labor Day rerun of Grit, first published Jan 9, 2023, the ServiceNow CEO reflects on what he learned from his earliest jobs and how he carried those lessons from a deli counter in Long Island to the boardroom of an $80B software company.

We cover:

How do you win when your competitors are the biggest companies in the world?

This week on Grit, Dropbox co-founder and CEO Drew Houston retraces the path from a bus-stop prototype to competing head-on with Google, Apple, and Microsoft.

He explains why grit is “learning to run toward discomfort,” and the moments he realized founders keep going “for the love of the game.”

Guest: Drew Houston, Co-Founder & CEO of Dropbox

Chapters:

00:00 Trailer
00:52 Introduction
01:35 Towards full autonomy
16:20 Coming back to school
21:45...

Even with AI, sales still comes down to human connection.

This week on Grit, Dan Lee shares how Nooks automates busywork like research and dialing for thousands of sales teams, letting reps focus on the conversations that close deals.

He also shares his “do more with less” approach, why cold calls still convert, and how to maximize human impact alongside AI.

Guests: Dan Lee, CEO and Co-founder of Nooks and Leigh Marie Braswell, Partner at Kleiner Perkins

Connect with Dan Lee: 

Connect with Leigh Marie Braswell

What if your tools shared context like your team does?

This week on Grit, Shishir Mehrotra shares how the Coda and Grammarly collaboration unlocks context as a “superpower,” reflects on his early days at Google and YouTube, and hints at a future where tools anticipate intent and amplify how we work.

He also shares how this paves the way for agent-based workflows and AI-native communication, beginning with Superhuman’s email experience.

Guest: Shishir Mehrotra, co-founder of Coda and CEO of Grammarly

Connect with Shishir

Chapters:
00:00 Trailer
01...

Ivan Zhao joins Joubin Mirzadegan on Grit to break down how the company’s minimalist design became a strategic edge in a world overwhelmed by bloated software. 

He shares why the AI agent still hasn’t arrived, and how Notion’s modular approach might be the closest thing to making it real.

Guest: Ivan Zhao, co-founder and CEO of Notion

Mentioned in this episode: Fuzzy Khosrowshahi, Airbnb, Sequoia Capital, Linear, Figma, Apple, Things, Microsoft, BMW, Lumiere, The Beatles, The Rolling Stones, Eric Clapton, Rippling, Matt MacInnis, Inkling...

How did Tripadvisor become every traveler’s starting point?

Steve Kaufer joins Joubin Mirzadegan on Grit to break down how Tripadvisor became the internet’s trusted travel companion, built on over a billion reviews and decades of trust. He also shares why early personalization fell short and how AI is finally doing what travel agents once did by understanding the traveler, but faster, smarter, and at scale.

Guest: Steve Kaufer, co-founder of TripAdvisor

Chapters:

(00:00) Trailer
(00:45) Introduction
(01:32) Early days of Tripadvisor
(08:14) Catching the startup bug
(18:42) Luck...

Guests: Garrett Lord, co-founder and CEO of Handshake; and Mamoon Hamid, partner at Kleiner Perkins.

Handshake set out to democratize career opportunity. In the process, it unlocked something more: a high-trust expert network built on verified talent and earned trust.

This week on Grit, Garrett Lord shares how what began as a platform for student job seekers is now partnering with leading labs, enabling experts to train real-world AI systems. He explains how owning verified domain talent has become their core strategic edge, bypassing middlemen and turning a decade of trust into lasting advantage.

Zach Perret saw a fintech explosion coming—and built the rails before it arrived.

On this week’s Grit, the Plaid co-founder and CEO retraces his path from building tools for developers to linking the world’s largest banks, and how a failed $5.3B acquisition by Visa became a launchpad.

He unpacks the pressure of operating in a tightly regulated industry, why rebuilding trust after the deal collapse was harder than expected, and how Plaid is navigating the shift from startup to staple—while staying obsessed with the end user.

Links:

Connect...

Six leaders from across tech — from SaaS and semis to law and logistics — come together for our 250th episode milestone in this very special AI recap, where we unpack how new advances are transforming the way industries function, and how work gets done.

Featuring:

• Bret Taylor (Sierra Co-founder)
• Winston Weinberg (Harvey Co-founder and CEO)
• Matt Murphy (Marvell Technology Chairman and CEO)
• Yamini Rangan (HubSpot CEO)
• Chris Urmson (Aurora CEO)
• Varun Mohan (Windsurf Co-founder and CEO)

Connect with Joubin:

- LinkedIn: https://www.linkedin.com/in/joubin-mirzadegan-66186854/ 
- X:  https...

Daragh Murphy is giving brands their own credit-card platform—no legacy bank required.

On this week’s Grit, the Imprint co-founder and CEO traces the leap from being a junior lawyer to closing nine-figure card deals.

He breaks down the hidden economics of credit-card loyalty, the discipline of treating capital “like the last dollar,” and how AI will slash risk-and-support costs.

Guest: Daragh Murphy, CEO & Co-Founder of Imprint

Chapters:
00:00 Trailer
00:48 Introduction
01:30 Actualizing the dream
08:37 Imprint
11:37 Partnerships are massive
16:48 Understand the market
18:42 “Get more, spend more...

Bill Staples has spent 30 years redefining how the world writes, ships, and secures code.

On this week’s Grit, the GitLab CEO shares what it takes to lead a public, all-remote DevSecOps company trusted by more than half of the Fortune 100.

He breaks down the discipline of managing energy instead of hours, why weekly operating cadences beat quarterly plans, and how AI will 10× software engineers by auto-debugging code and closing security gaps.

Guest: Bill Staples, CEO of GitLab

Chapters:

00:00 Trailer

00:42 Introduction

02:34 True joy in life

What does it take to build the logistics backbone for the next generation of commerce?

Sean Henry, founder and CEO of Stord, joins Kleiner Perkins partner Ilya Fushman and Grit host Joubin Mirzadegan to talk about scaling a national fulfillment network that now moves 50 million packages a year and reaches 15% of U.S. households.

They explore how Stored is using AI to connect warehouses, middle-mile routes, and delivery promises into one smart system. The goal: to give every brand an Amazon Prime-like advantage.

Guest: Sean Henry, Co-Founder & CEO of Stord<...

Eric Yuan turned a simple belief into Zoom, the platform that kept the world moving through a once-in-a-century shutdown and redefined modern work. 

On this episode of Grit, the Zoom CEO shares why velocity beats size, how a family-first ethos powered his leadership during COVID, and why the coming wave of AI dwarfs the original internet boom. 

He details how he’s refreshing Zoom’s culture for 7,500 people, opting for virtual deal calls over in person meetings, settling into life as an empty-nester, and keeping Zoom nimble enough to outpace Big Tech and the next wave o...

Over the past two decades, Bret Taylor has quietly helped shape the arc of Silicon Valley.

From co-creating Google Maps to steering Facebook, Salesforce, and OpenAI, he’s been behind some of the most consequential products in tech. Now, with his new company Sierra, he’s starting from zero—again.

In this conversation, Bret opens up about how founders navigate identity, why the best ideas often come from everyday friction, and how staying relentlessly focused can unlock real momentum in AI.

Guest: Bret Taylor, Co-Founder of Sierra

Chapte...

Chris Urmson has spent the last 20 years pushing the limits of autonomous driving—first at Carnegie Mellon’s DARPA Grand Challenge team, then as co-founder of Google’s self-driving car project, now Waymo.

On this week’s episode, the Aurora CEO retraces that journey—from building robot cars in the desert to leading a public company pioneering driverless trucking.

He shares why autonomy was always a matter of when, not if, how he handled a high-profile departure from Waymo, and what it takes to build at the intersection of deep tech, safety, and infrastructure.

Now eigh...

John Chambers led Cisco through the rise of the internet—transforming it into the world’s most valuable company at its peak.

On this week’s Grit, the former Cisco CEO unpacks how he scaled the business from $70M to $50B+, pioneered M&A as a growth strategy with 180 acquisitions, and built what many called the best sales force in tech.

Now leading his own venture firm, Chambers shares how he’s backing the next generation of AI-native startups.

Guest: John T. Chambers, Former Cisco Executive Chairman & CEO, JC2 Vent...

Matt Murphy transformed Marvell from a broad-based chip supplier into a $100B data infrastructure leader—powering the rise of AI, cloud, 5G, and custom silicon.

On this week’s Grit, the Marvell CEO shares how he refocused the company’s strategy, led major acquisitions like Inphi ($10B) and Cavium ($6B), and positioned Marvell at the center of the next era of compute.

He also reflects on lessons from his father, a longtime CEO, the discipline of running 90 miles a week, and how staying steady through industry cycles has set him apart.

Chapters:
00:00 Traile...

From a 350-square-foot home in South India to leading HubSpot, a $30B CRM powerhouse, Yamini Rangan’s journey is nothing short of remarkable.

In this episode, Yamini shares how she’s guiding HubSpot through a post-pandemic shift toward product-led growth, the hard-won lessons behind building go-to-market alignment, and why human-centric leadership is her edge in an AI-first world. Plus, her take on why data is the new battleground in tech.

Chapters:
00:00 Trailer
00:52 Introduction
02:22 Fire in my belly
10:06 Constraints
12:19 Peak performance
16:38 Helping while in sheer panic
21:43 The general ethos
3...

David Rubenstein helped pioneer modern private equity—building The Carlyle Group into a $400B global investment firm from a modest D.C. office and a relentless fundraising streak. But beyond PE, his legacy spans presidential libraries, historic American artifacts, and a lifelong obsession with civic contribution.

In this episode, David shares how he raised billions without a background in finance, why owning a baseball team was more than just a trophy purchase—and what building true generational success really means beyond wealth alone.

Chapters:
00:00 Trailer
00:53 Introduction
01:40 Family, wealth, class
14:40 Happiness disparity and...

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 13-year-old codebase, why analytics remains Amplitude’s competitive edge—and why taking the company public early was a risk worth taking.

Chapters:
00:00 Trailer
00:43 Introduction
01:26 AI is still very early
05:48 The urgency of building from the ground up
08:49 Bringing in new blood<...

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 weighs in on Trump’s proposed tariffs and what they could mean for the future of global tra...

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, faster growth.

Chapters:
00:00 Trailer
00:46 Introduction
01:45 Startup roller coaster
05...

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 the company’s next big AI bet.<...

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 OpenGov’s earliest days, and that mission has informed everything from hiring to M&A to the decision to...

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 level of stress a CEO might have. Adopti...

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 his lifelong love of aviation. He began educating himself about things he had never thought to learn, and tapping his LinkedIn network...

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 ... It was a really all-consuming effort to get the company...

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 of lawyers. Instead, he says, they need to have “respect for the industry” be...

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 Wolt, and what I do today,” Miki says. “That's where I learned most of the core lessons that I put into acti...

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 to Bobby than Microsoft. Concerned about his ability to get...

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 with the magician Nate Staniforth on a new rest...

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 was the transition from running a weap...

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 agency.

“Well-regarded CEOs from TradFi, they were like, ‘You don’t do that,’” Emi...

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 companies like Lattice should loo...

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, managerial over-hiring, and sloppy scheduling prevents people from reaching a flow state.

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:

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, managerial over-hiring, and sloppy scheduling prevents people from reaching a flow state...

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 an even bigger project, developing an entire neighborhood near Oracle called Mission...

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, something that has served Tony well across hi...

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 we know where we are,” Jeff says.

“If we’re perfect in it, compounding over...

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 order is this paragraph called the commander's intent,” he explai...

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 ha...

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 talent is concentrated there. 

“When you hire someone that’s 10x better,” he says, “yo...

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, but previously thought to be unscalable — could shift the educational bell curve “s...

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 their plane’s engine and aerodynamics. 

“You can’t be...

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 startup, Amazon.com, which elicited “this awesome laugh, the Jeff Bezos trademark laugh.” How a leader...

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 the Loom employees, current and former, t...

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 undeterred. The way he describes today’s leading AI powers sounds like an i...

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 going to be the busiest man in the wo...

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 underwent before signing KP’s term sheet. “It's pretty rare for a founder's...

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 probably communicated more with [my wife...

Guest: Jack Conte, CEO & co-founder of Patreon

For many YouTube video creators, getting millions of views on your videos may seem like the goal. But when Jack Conte and his wife Nataly Dawn became YouTube stars through their band Pomplamoose, they didn’t automatically find gold at the end of the rainbow.

“You check your ad revenue and you make 48 bucks in ad revenue and you're like, ‘Oh my God, I'm worthless,’” Jack recalls. “And you check that dashboard every day ... and eventually you start to believe that you're worth $48 a month. That's a bad f**king feel...

Guest: Mark Pincus, founder & chairman of Zynga, and managing member & co-founder of Reinvent Capital

Before Zynga and Facebook made social gaming mainstream, the video game industry was “extreme on this being about art and crafting,” recalls Zynga founder Mark Pincus. He believes his winning instinct was the realization that games were “at least 50 percent science” — but it’s not enough to just have the instinct. 

Mark says entrepreneurs like him have to quickly take multiple shots on the goal and “look for feedback loops that tell you your instinct is right ... you need to get to a minimum vi...

Guest: RJ Scaringe, CEO and Founder of Rivian

“I’m very comfortable with things not being in their end state,” says Rivian CEO and founder RJ Scaringe. The company’s challenging mission — to help make 100% of the world’s cars electric — will take a long time, and a lot of willingness to build the metaphorical plane in midair. 

As Rivian has grown from one person to seven to 17,000, though, RJ admits that there’s a lot more pressure to not screw up. “There’s all these conflicting emotions I had ... is this the right product?” he recalls. “Is it the...

Guest: Sridhar Ramaswamy, CEO of Snowflake

“People underestimate what it is to go through a complete reset,” says Snowflake CEO Sridhar Ramaswamy. And he knows it: After an incredible 15-year run at Google, he started over from zero with an AI search startup, Neeva. And in hindsight, he regrets not trying to port over more of the skills that had made him a successful leader before. “You should be truthful with yourself about what is it that you know that you're really good at,” he says.

In this episode, Sridhar and Joubin discuss Morgan Stanley, working...

Guest: James Freeman, Founder and Former CEO of Blue Bottle Coffee

In the six or so years since he sold his last shares of Blue Bottle Coffee to Nestlé, James Freeman has had a lot of time to ruminate — about how he succeeded in creating a unique café experience, and also the ways he failed his workers as a manager. But he’s already thinking about how he’ll be better in round 2.  “I've changed so much — physically, mentally, emotionally — I feel like I could be a better collaborator,” James says.

In this episode, James and Joubin discus...

Guest: John Hanke, CEO of Niantic

When Pokémon Go launched, Niantic CEO John Hanke was enjoying a tranquil walk through a bamboo forest near Kyoto with his son. When he got back, it was all hands on deck: Building on a platform Niantic had developed for its previous game, Ingress, Pokémon Go was a runaway success story, earning $100 million dollars in revenue in its first week, and $1 billion in its first seven months. “I had a huge amount of anxiety that this is just too good to be true,” John recalls. “When are the wheels going to...

Guest: Mark McLaughlin, chairman of the board at Qualcomm 

When he was 24, Mark McLaughlin thought his career was over. Since childhood, he had dreamed of attending West Point and joining the Army, but a helicopter crash left him unable to serve, with a medical discharge. However, the crash also let him stay closer to his then-girlfriend Karen. They married and raised three children, and Mark found success in his new career, serving as CEO of Palo Alto Networks and now chairman of the board at Qualcomm. “In hindsight,” he says, “I would tell you the worst thing that ev...

Guest: David Risher, CEO of Lyft

David Risher can measure his career in phone calls, from the one that introduced him to Jeff Bezos in 1995, to the call from the Lyft board in 2023, asking him to vie for the CEO job. But initially, he believed his life’s legacy might be the nonprofit Worldreader, which has brought books to more than 22 million readers around the globe; he had to convince himself that turning Lyft around during one of its most difficult eras was also a call worth answering.

In this episode, David and Joubin discuss re...

Guests: Vipul Ved Prakash, CEO and co-founder of Together AI; and Bucky Moore, partner at Kleiner Perkins

No one knows for sure whether the future of AI will be driven more by research labs and AI-native companies, or by enterprises applying the technology to their own data sets. But one thing is for sure, says Together AI CEO and co-founder Vipul Ved Prakash: It’s going to be a lot bigger. “If you look at the next 10 years or the next 20 years, we are doing maybe 0.1 percent of [the] AI that we’ll be doing 10 years from now.” ...

Guest: Andrew Bialecki, CEO of Klaviyo

Whenever the marketing platform Klaviyo is hiring, says CEO Andrew Bialecki, “we sort of don't care so much what skills you have.” Instead, the company looks for “high slope” individuals who are curious and able to continually learn new things. “A big turnoff for me is [when] somebody says, ‘Oh, well, I was never good at that when I was growing up,’” Andrew explains. “You know, ‘I'm not a good writer’ or ‘I'm not good with numbers.’ And it's like, well, OK, but anybody can learn anything.”

In this episode, Andrew and Joubin d...

Guest: Niraj Shah, CEO and co-founder of Wayfair

Wayfair CEO Niraj Shah caught the entrepreneurship bug in his mid-20s, when he and his longtime co-founder Steve Conine sold their first company just a few years out of college. They left the acquirer and independently realized “we absolutely wanted to start something else,” Niraj recalls. “Once you’ve done that, if you enjoy that, it’s very hard to pursue something more traditional.” But the “if you enjoy that” bit really matters: Whenever he’s counseling younger people, Niraj tells them to pursue something they’re genuinely excited about. Other...

Guest: Jay Chaudhry, CEO, chairman, and founder of Zscaler

Much of the media coverage of Zscaler CEO Jay Chaudhry is quick to identify him as the wealthiest Indian-American person, with a net worth of $10.8 billion. But to hear Jay himself tell it, that number has never been very important to him: “My family had no money,” he says of his childhood in India. “I had no attachment for money. There was no feeling of ‘I must buy this, buy this.’ ... And it hasn’t changed a bit.” Perhaps surprisingly, he says not caring about money is one of the big rea...

Guest: Bill Magnuson, CEO and co-founder of Braze

The deployment of smartphones around the world was more impactful than any other technology to date, says Braze CEO Bill Magnuson — and that has big implications for emerging fields like generative AI. “If we get to the point where they [LLMs] really can be useful, human-like companions ... they will be usable by everyone that has smartphone technology.” In other words, the question is not business opportunity or scale: It’s capability.

In this episode, Bill and Joubin discuss earnings days, Aaron Levie, MIT, customer churn, shower thoughts, technica...

Guest: Clara Shih, CEO of Salesforce AI

In 2020, Clara Shih quit Hearsay, the company she founded and ran for 11 years; in hindsight, she says “I probably should have quit a little bit sooner.” But at the time, she cared a lot — too much — about what everyone else thought. “There's a lot of guilt around leaving initially and feeling bad for feeling bad,” Clara says. But her worries subsided when her replacement and former COO, Mike Boese, guided the company with “class and grace” to an exit: A $125 million+ acquisition just this week by Yext.

In this episode, Cl...

Guest: Marissa Mayer, CEO and Founder of Sunshine and former CEO of Yahoo

When Marissa Mayer was first hired as the CEO of Yahoo, the company had lost nearly a quarter of its workforce in the preceding six months. Early on, she was chatting with employees in the cafeteria and one of them got her attention by smacking her tray. “Is it go time?” he asked. He was asking if the board and C-suite were ready to lead the company forward, but Marissa thought he had one foot out the door. “I had just come out of this m...

Guest: Sarah Friar, former CEO of Nextdoor

Sarah Friar has worked with some of the top leaders in Silicon Valley, including Salesforce CEO Marc Benioff, Walmart CEO Doug McMillon, Block CEO Jack Dorsey, and most recently Nextdoor founder Nirav Tolia, who just replaced her as CEO in May. And one of the things that sets top performers apart from the rest, she argues, is their compassion and their responsiveness. When her former EA’s husband was diagnosed with cancer, Sarah texted Benioff — who she had just left behind to work at Square — for help. Within seconds, she recall...

Guest: Stanislav Vishnevskiy, CTO and co-founder of Discord

For many years, the conventional wisdom was the gaming was not social because it was something you usually did at home. “But people who play games are often the most social,” says Discord CTO Stanislav Vishnevskiy. “They’re spending 10, 20 hours with other people online, hanging out.” As a teenager, Stanislav logged more than 1,000 days playing his favorite video game and socializing with friends around the world, but with 200 million monthly active users, the social platform is appealing to a lot more than hardcore gamers. “People online who need to get together...

Guest: Eoghan McCabe, CEO, Chairman, and Co-Founder of Intercom

“We are not ready for the degree to which our world is going to change,” says Intercom CEO Eoghan McCabe, “in insane and incredible ways.” When he co-founded the company in 2011, the Irish-born entrepreneur was making it easier for companies to offer human customer service to their customers. But Eoghan believes “every single type of knowledge work” will soon be done by AI, and Intercom is well on its way to that destination: 45 percent of all tickets are being answered by bots now, and he expects that number to climb to...

Guest: Mark Cuban, co-founder of Cost Plus Drugs and costar, Shark Tank

“I just love to compete,” says Mark Cuban. “And the day I stop is the day I’m dead.” Previously the co-founder of MicroSolutions and Broadcast.com, Cuban is probably best known to the public today for competing with the likes of Daymond John and Barbara Corcoran on the reality TV show Shark Tank. But his real focus — and his real enemy — these days is the pharmaceutical industry. His latest company, Cost Plus Drugs, aims to be far more transparent than established PBMs, or Pharmacy Be...

Guest: Taylor Francis, co-founder of Watershed

One day when he was 13, Taylor Francis walked out of the movie theater, and he was pissed off. He had just seen Al Gore’s documentary An Inconvenient Truth and internalized a “generational call to arms, that my parents had screwed our generation” by causing the climate crisis, he says. 14 years later, he was working at Stripe and felt another call to arms: The 2020s would be a crucial decade for slashing carbon emissions and combating global warming. So, he and his co-founders Avi Itskovich and Christian Anderson all left Stripe to sta...

Guests: Victor Riparbelli, CEO and co-founder of Synthesia; and Josh Coyne, partner at Kleiner Perkins

When Victor Riparbelli wants to learn something, he’ll start with a YouTube video or a podcast: “I maybe buy the book on Amazon as like the fifth step,” the Synthesia CEO says. His company is trying to change the text-first (or text-only) way information is conveyed at work, making AI avatar-narrated videos to replace documents like customer profiles and HR manuals. Victor says that as the technology improves over many years, it could replace text entirely. “I think for most people, if they...

Guest: Kat Cole, COO of Athletic Greens

You can’t make smart decisions if you don’t know the truth — the “true truth,” as Athletic Greens COO Kat Cole puts it. “As you get bigger and you have success, innovator’s dilemma, you end up talking to yourself instead of really being rooted in what’s going on.” That’s why she has embraced the anxiety of the unknown, channeling what she doesn’t know about the market into productive questions for her team and her customers. Anxiety can be harmful, she concedes, but “there’s a healthy version of believi...

Guest: Anne Raimondi, COO and Head of Business at Asana

Asana COO Anne Raimondi feels pressure to perform in her job “every day, all the time.” But that pressure doesn’t come from her fellow executives; she imposes it on herself, trying to think carefully about how much each of her decisions will impact her team. “I have a lot of privilege and choice,” Anne says, “of how I spend my time, the resources available to me, and am I doing enough? ... Am I doing the most with the opportunities I have, and making as positive an impact as I...

Guest: Sanjay Beri, CEO and Founder of Netskope

“You can be waiting your whole life to do something, and then your life’s over,” says Sanjay Beri. After nine years at Juniper Networks, he left his comfortable job, moved his family to a house with a pricier mortgage, and launched the cloud security firm Netskope. His entrepreneurial story would make anyone stressed, he acknowledges, but “at some level, you have to be wired to enjoy it… that's why I tell everybody who joins, ‘It's not for the faint of heart.’”

In this episode, Sanjay and Joubin discuss R...

Guest: Scott McNealy, former CEO and co-founder of Sun Microsystems & co-founder of Curriki

Scott McNealy never wanted to be CEO of Sun, and in his 22-year tenure before selling to Oracle, he knows there were times he failed to execute, or to rein in the once-iconic Silicon Valley firm’s worst impulses. But like his pro golfer son, Maverick, Scott doesn’t like to look back: “Golfers will always look back and blame the wind, a divot that wasn't repaired, a bad rake job, a mower cut that wasn't done properly, a gust of wind,” he explains. “If you bla...

Guest: Jyoti Bansal, CEO and co-founder of Harness

Cisco bought Jyoti Bansal’s first company AppDynamics for $3.7 billion, making him a very wealthy man. But after two African safaris, a week of Michelin-starred meals in Tokyo, and more adventures all around the world, he realized that spending his money didn’t truly make him happy. After some soul-searching, he realized what he really enjoyed: “I liked to build companies. That is my craft ... If someone enjoys playing gold for six hours, I would enjoy working on a startup for six hours.”

In this episode, Jyoti and Joub...

Guest: Clint Sharp, CEO and co-founder of Cribl

New employees are joining the remote data platform Cribl every week, and as the staff grows, CEO Clint Sharp has noticed a problem: He can’t file a bug report without a lot of caveats. When there were a handful of users, no one would bat an eye at the CEO posting a bug on Slack, but now he has had to learn how to phrase things because people assume he’s “irate and we should change everything we’re doing,” Clint says. “I’ll post something and there’s a flurry of DM...

Guest: Glen Tullman, CEO of Transcarent

Before he was CEO of Transcarent, Glen Tullman presided over the biggest digital health merger of all time: His previous company Livongo was acquired in 2020 by Teledoc for $18.5 billion. Over his decades of experience in health tech, he has developed saying: Hire low, fire high. When one of his friends was offered a job and said he wanted to consider another offer, Glen withdrew Transcarent’s offer because he didn’t want to be the highest bidder — in other words, hire low. But whenever he has to let someone go, he sees i...

Guest: Filip Kaliszan, CEO and co-founder of Verkada

Great founders try to grow personally at least as fast as their companies do — but sometimes, says Verkada CEO Filip Kaliszan, that’s just not possible. By the time the company had about 200 employees, he says, “the scale of the business and the rate of the growth of the business ... outpaced my rate of learning, or my ability to consult the right people.” But over time, he has worked to fix past errors and earn everyone’s trust: “I can be only as good as the rate at which I fix my mis...

Guest: Wade Foster, CEO and co-founder of Zapier

When Wade Foster and his co-founders launched Zapier, he was 24, and doubted himself constantly. He consulted mentors like Paul Graham and Jay Simons, studied entrepreneurs like Jeff Bezos and Steve Jobs, and also took inspiration from an unlikely source: Actor and martial artist Bruce Lee. “[He] had this fighting style, ‘The Way of No Way,’” Wade says. “He would study all the different fighting styles, and he would say, ‘None of them is the best or the worst ... My job was to take the best of each and then discard the...

Guest: Kim Scott, author of Radical Candor: Be a Kickass Boss Without Losing Your Humanity and Radical Respect: How To Work Together Better

After her first management book Radical Candor became a worldwide bestseller, Kim Scott found herself giving talks to all kinds of companies about how they could apply her advice and build a stronger, kinder culture. But then, after one such talk, the CEO — a longtime friend and former coworker — came up to Kim with an asterisk. As a Black woman, she explained, “as soon as I offer anyone even the most compassionate, gentle...

Guest: Daniela Amodei, President and co-founder of Anthropic

With a reported valuation of as much as $18 billion, Anthropic has the resources to be one of the dominant AI companies in Silicon Valley; however, it was conceived as a public benefit corporation and always tries to strike a balance between hypergrowth and responsibility. Anthropic’s flagship LLM, Claude, must adhere to a “constitution” of values that prioritize the good of humanity. And even though every company wants to “do AI” right now, President Daniela Amodei says some of them should slow down. “I keep coming back to this idea of, ‘Ho...

Guest: Dev Ittycheria, CEO and President of MongoDB

When you think about who you were and the decisions you made two, or four, or eight years ago ... how do you feel? Dev Ittycheria, the President and CEO of MongoDB, says he’s embarrassed about certain things he did — and that’s a good thing. “If you’re not [embarrassed], that means you’re not really growing that fast,” he says. He recalled one of his mentors, former BladeLogic chairman Steve Walske, explaining that everyone has an overinflated opinion of themselves, and the great leaders keep the gap between that o...

Guest: Frank Slootman, CEO and Chairman of Snowflake and author of Amp It Up

Snowflake CEO Frank Slootman doesn’t recall a time in his childhood where new achievements were celebrated — because, according to his father, putting everything into your work and “leaving it all on the field” was the only choice. “The problem with it,” Frank says, is that “it becomes a ‘never enough’ dynamic, because when is it enough?” To this day, he comes home on Friday night and asks himself, “Did it mater that I was there? ... If I’m just a passenger on the ship, t...

Guest: Jason Kelly, CEO and co-founder of Ginkgo Bioworks

Almost everyone in the second generation of biotechnology entrepreneurs, says Ginkgo Bioworks CEO Jason Kelly, works in that field because of one thing: Jurassic Park. The Michael Crichton novel-turned-Steven Spielberg movie captured both the wonder and beauty of bioengineering, and the challenges of bending DNA to your own ends. “You didn’t invent biology,” Jason says. “You need to have humility in the face of it ... because life will find a way. It will do things you don’t expect. It’s not a computer.” 

In this episode, J...

Guest: John McMahon, author of The Qualified Sales Leader: Proven Lessons from a Five Time CRO

A hell of a lot of people work in sales. But until recently, says five-time CRO and The Qualified Sales Leader author John McMahon, it was rare for colleges and universities to offer a sales degree. Salespeople had to learn on the job from experienced coaches, and adapt. And their bosses, John explains, had to themselves as agents of transformation. “If somebody’s really smart, they’re going to pick up the knowledge,” he says. “If they have what I call a P...

Guest: Angela Duckworth, professor at the University of Pennsylvania and author of Grit: The Power of Passion and Perseverance

“There’s got to be a cost” when you pursue your passions, says University of Pennsylvania professor Angela Duckworth; in fact, the word “passion” comes from the Latin word for “suffering.” But that doesn’t mean that gritty people are unhappy. After the time needed for sleep, daily exercise, friends, and family, Dr. Duckworth explains, “what’s left is more than 40 hours.” Informed by her research and her own happiness, she tries to discourage her students from settling for a 9...

Guest: David Cancel, founder and former CEO of Drift; founder of Rey

After HubSpot acquired his company Performable in 2011, David Cancel became his acquirer’s Chief Product Officer — and didn’t give any thought to how long he’d be in that role. When he started eyeing the exit a few years later, he was told that wasn’t an option: HubSpot had already filed to go public, and an officer of the company leaving in the first 18 months would raise major red flags. “Maybe this is what’s led me to be an entrepreneur,” David recalls. “I can never feel t...

Guest: John Doerr, chairman of Kleiner Perkins

After Kleiner Perkins chairman John Doerr first invested in Google — $12.8 million for 13 percent of the company — he told co-founders Larry Page and Sergey Brin that they needed to hire a CEO to help them build the business. After they took meetings with a variety of successful tech execs, they came back to Doerr and told him “We’ve got some good news and some bad news.” The good news was that they agreed on the need for a CEO; the bad news, Doerr recalls, is that they believed there was only one p...

Guest: Shlomo Kramer, founder and CEO of Cato Networks

Shlomo Kramer has founded three companies to date — Check Point, Imperva, and most recently Cato Networks — and taken the first two public, with plans to do the same with Cato. By any measure, he is a successful entrepreneur, but he defines “success” as “a burden you need to shake off every day.” And the easiest way to do that he’s found is to keep moving, keep failing, and keep creating. The material wealth he’s created, he explains, was never the goal: “It was never about things. It was about ideas...

Guest: Arvind Jain, Founder and CEO of Glean, and Mamoon Hamid, partner at Kleiner Perkins

“I’m an engineer, so I have doubts about everything,” says Glean founder and CEO Arvind Jain. Well ... almost everything. Since launching Glean in 2019, he has held to the belief that “all of us are going to have really powerful AI assistants” in the future. With a several-year lead on generative AI tools like ChatGPT, Glean has built a growing club of CIO fans. With the broad acceptance of AI over the past year, Arvind says, “the level of confidence is higher than ever be...