Grit
Grit is a podcast about what it takes to create, build, and scale world-class organizations. Each week it highlights leaders who are pushing their companies to make a difference. The series is hosted by Joubin Mirzadegan, a go-to-market operating partner at the venture capital firm Kleiner Perkins. It focuses on the strategies and experiences behind building impactful companies.
Episodes
Inside the AI Startup Making Customer Support 65% Cheaper
How do you keep up when you go from 50 to 500 employees in a year?Jesse Zhang shares how Decagon scaled that quickly, from hiring ahead of demand to keeping the company connected as the team grows.He also explains why the zero-to-one phase is so different from scaling, and how Decagon found its way out of the idea maze in just three weeks.Guest: Jesse Zhang, Co-founder and CEO, DecagonCon
The AI Race Has a Leaderboard | Arena CEO Anastasios Angelopoulos
AI could be bigger than electricity.Anastasios Angelopoulos is seeing that shift firsthand, with Arena ranking 500+ models and tracking roughly 10 new releases every week.On Grit, he explains why there may never be one dominant AI model and why the API layer may be less sticky than people think.Guest: Anastasios Angelopoulos, Co-Founder and CEO of ArenaConnect with Anastasios Angelopoulos
Data Centers in Orbit by 2028: Baiju Bhatt on His Plans After Robinhood
What kind of founder walks away from a multi-billion-dollar fintech company to start building rockets?Baiju Bhatt, co-founder of Robinhood, joins Joubin Mirzadegan to talk about life after one of the most consequential companies in modern finance, and why he's now betting on Cowboy Space Corporation, an orbital infrastructure company building AI data centers that ride to space inside its
Booking.com CEO on AI and the Future of Travel
"Our mission is to make it easier for everybody to experience the world."From the dot-com crash to AI, Glenn Fogel has spent nearly three decades helping Booking Holdings evolve through every major technology shift while staying true to that mission.He also shares with Joubin Mirzadegan why "you're always selling," and how Booking is using AI to amplify what every employee can accomplish.
Ex-Twitter CEO on Why AI Needs a New Internet | Parag Agrawal
"The answer to every problem is a model."Parag Agrawal shares the ideas behind Parallel: products that continuously learn, and teams designed around versatile problem solvers.He also shares why he built an AI agent for himself, and why AI's biggest opportunity is expanding what people can achieve.Guest: Parag Agrawal, founder and CEO of Parallel, and former CEO of TwitterConnect with Para
The Sales Framework Every Founder Needs | Mark Roberge
"There's 20 fires going on at every moment in the office and you have enough water to put out four."Mark Roberge shares what it takes to build and scale a company, from finding product-market fit to knowing when it's time to grow.He also shares the framework behind his new book, The Science of Selling, and why founders should scale based on their own data, not another company's success.Gu
Airwallex's Jack Zhang on Fintech, Failure, and Growth
In 2020, Airwallex lost nearly half its revenue overnight. Today it's worth $11 billion.Jack Zhang reflects on the decisions that kept the company alive, raising capital during uncertainty, and leading through its toughest chapter.This episode is a candid look at why Jack chose to keep building, even when a $1.2 billion acquisition was on the table.Guest: Jack Zhang, founder and CEO, Airw
Why 80% of the Fortune 100 Chose Qualtrics | Ryan Smith
AI may change software overnight, but company building still takes time.Ryan Smith explains why, despite the pace of AI, “the race is going to be way longer than anyone thinks.”He reflects on Qualtrics surviving multiple market cycles and ultimately being acquired by SAP for $8 billion days before going public.Guest: Ryan Smith, co-founder QualtricsConnect with Ryan SmithXLinkedInConnect
What It Takes to Build Software for 171,000+ Restaurants | Aman Narang
Great software companies often come from understanding pain points at a very deep level.On Grit, Aman Narang shares how Toast built trust with 171,000+ restaurant operators by helping restaurants manage everything from payments and online orders to staff scheduling and daily operations.He also reflects on lessons around product-market fit and scaling a company before it’s fully ready.Gues
What It Takes to Build a Generational Company | Anduril’s Trae Stephens
Founder quality becomes more important as startups become easier to build.Trae Stephens, co-founder of Anduril and partner at Founders Fund, has spent years backing founders with strong conviction, including most recently at Roadrunner.He shares why too much capital too early can hurt startups, and why the best companies are built by teams with complementary strengths.Guest: Trae Stephens
How AIG Is Reinventing Insurance With AI | Peter Zaffino
What does it take to run a company where the business is risk itself?In conversation with Joubin Mirzadegan, Peter Zaffino shares what the role demands at AIG, including high stakes decisions, constant responsibility, and sacrifice. This episode looks at his journey as CEO ahead of his transition to Executive Chairman this June.Leading at a global scale across 200+ countries.Guest: Peter
From Airbnb to Linear: How Karri Saarinen Redefined Product Design
In a market that hadn’t changed in decades, Linear didn’t win by being faster. They won by being more thoughtful.Karri Saarinen helped shape design at Airbnb and Coinbase before building Linear around small teams and high standards.On Grit, he shares how Linear is building for a new era of software development.Guest: Karri Saarinen, co-founder and CEO of LinearConnect with Karri SaarinenX
How Kevin Mandia Built the Most Trusted Name in Cybersecurity
What does security look like when attackers use AI better than you do?Armadin recently raised $200M to build for the “attacker of the future,” where attacks are autonomous and harder to contain.On the Kleiner Perkins Grit podcast, Kevin Mandia joins Joubin Mirzadegan to share how he’s thinking about this shift, why cybersecurity has always been a calling, and why customer trust is what ul
The Silicon Valley Insider In The Pentagon | DoW Emil Michael
Emil Michael went from scaling Uber across 600 cities to rewiring the world's largest military.In the midst of the Pentagon-Silicon Valley debate, the now U.S. Under Secretary of Defense for Research and Engineering opens up about what a real partnership demands from both sides.He also shares how he's built three new entry points for defense tech companies, and why America's military is c
How Sierra Is Pulling Ahead in the AI Race | Co-founder Bret Taylor
Few founders have seen Silicon Valley from every seat at the table.After co-creating Google Maps at Google, serving as CTO at Facebook, and later as co-CEO of Salesforce, Bret Taylor is now building AI agents at Sierra to redefine customer experience.On Grit, he explains why “competitive intensity” is a core value at their fast-growing company and why he believes AI won’t lead to a world
The AI Era of Cybercrime: How Malwarebytes Is Evolving Its Security Stack | Marcin Kleczynski
What began as a 14 year old fixing infected computers became Malwarebytes, an 800 person cybersecurity company trusted by millions of customers.On Grit, Marcin Kleczynski joins Joubin Mirzadegan to explore AI driven cyber threats, strategic reinvention, and the discipline of evolving before the market forces you to.“We’ve exceeded. Now, what do we do to protect individuals against the nex
The Truth Behind Automation Claims in Customer Support | Cresta CEO Ping Wu
Can you scale customer support without burning out agents or frustrating customers?Ping Wu shares how Cresta combines AI and human intelligence into a single system that scales sustainably for companies like United Airlines and Porsche.In this episode, Ping also breaks down the three constraints that shape automation in the real world: conversation complexity, infrastructure debt, and cus
The Safest Dollar on the Internet | Circle CEO Jeremy Allaire
USDC closed the gap between software and law in modern finance.On Grit, Jeremy Allaire discusses how fully reserved, dollar backed digital currency became part of the financial system after more than a decade of work.He also shares why for him grit is about sustaining belief through deep uncertainty, even when Circle faced the threat of bankruptcy in 2019.Guest: Jeremy Allaire, Co-Founder
Why We’re Only Using 1% of AI | Glean CEO Arvind Jain
Glean has grown into a $7.2B company by giving employees AI assistants and agents that extend their capabilities.CEO Arvind Jain is back on Grit alongside Joubin Mirzadegan. Here’s what stood out:“My mindset by default is that if you build something last year, that it's got to be obsolete. There has to be a new way to do that thing better today. If not, then it's just lack of imagination.
The Grittiest Conversations of 2025: AI, Business & Beyond
In this recap episode, we highlight the best moments from our 2025 interviews and reflect on the ideas that defined the year.Featuring:David Rubenstein (co-founder of Carlyle) Yamini Rangan (CEO of HubSpot) Ben Chestnut (co-founder of Mailchimp) Winston Weinberg (co-founder and CEO of Harvey)Garrett Lord (co-founder of Handshake) Aidan Gomez (co-founder and CEO of Cohere) Michelle Zatlyn
How Brands Stay Visible When AI Decides | Profound CEO James Cadwallader
What happens when AI becomes your most influential referrer?As consumers turn to ChatGPT for answers, James Cadwallader and his team at Profound help brands like Eight Sleep and MongoDB gain visibility and leverage inside AI models.On this episode of Grit, he explains why brand narrative has shifted away from content, and why Profound is scaling globally ahead of traditional SaaS timeline
How Snap Plans to Win the AR Race | Evan Spiegel on Spectacles
Turning down a $3B offer from Facebook is a bold move for any young CEO.Evan Spiegel shares how Snap’s early dream was to stay independent and give its community an authentic voice, a bet that proved right.He also explains why they are now doubling down on AR glasses and why the anxiety around AI deserves far more attention from tech leaders.Guest: Evan Spiegel, co-founder and CEO of Snap
The Pull to Build: Joubin Mirzadegan on Grit and Starting Roadrunner
What does it take to go from advising founders to becoming one?On this week’s special Reverse Grit episode, we flip the script and put our Grit podcast host Joubin Mirzadegan in the guest seat.Joubin recently founded Roadrunner, where he is now co-founder & CEO. Roadrunner is building an AI‑native CPQ to modernize the quote‑to‑cash stack, drawing on years of conversations he’s had wit
Building Cloudflare for the Next 50 Years | Co-founder Cloudfare Michelle Zatlyn
Fifteen years in, it can still feel like “we’re just getting started.”Michelle Zatlyn, co-founder of Cloudflare, returns to Grit with Joubin Mirzadegan to share how Cloudflare secures the internet for millions, with a vision built to last generations.She also shares why staying close to reality and to customers becomes harder as success compounds, and how Cloudflare is helping content cre
She Sold Her Startup for $500 Million, Here’s Her Next Idea
Screens have pulled families apart. Brynn Putnam set out to bring them back together with Board, the world’s ‘first face-to-face game console.’On Grit, she tells Joubin Mirzadegan how every venture she’s built, including Mirror, started as a personal need, and how her true edge is the ability to strip an idea down to what actually matters.Guest: Brynn Putnam, founder and CEO of BoardConne
Synthetic Data and the Future of AI | Cohere CEO Aidan Gomez
How do companies like Salesforce and Dell scale intelligence across every cloud?Aidan Gomez, co-founder and CEO of Cohere, explains how they’re building AI that works across all enterprise systems and deploys anywhere, giving companies true flexibility and security.He joins Joubin Mirzadegan for a wide-ranging conversation on why synthetic data went from dismissed to indispensable, and ho
From Yext to Roam: Howard Lerman’s Second Act
The hardest company to build is the one you start after you’ve already succeeded.After scaling Yext into a platform powering millions of businesses, Howard Lerman chose to start over with Roam, the “Office of the Future,” where humans and AI work side by side from anywhere.On Grit, he joins Joubin Mirzadegan to talk about the solitude of leadership and what happens when you stop building
Rebuilding Front for the AI Era | CEO Dan O’Connell
The hardest part of transformation is knowing what to let go of.Dan O’Connell, now leading Front as CEO and formerly on the board at Dialpad, joins Joubin Mirzadegan to explore the delicate balance between legacy and innovation as he leads a decade old company through the AI revolution.He also reflects on why courage and control can coexist in leadership, and what it means to “make decisi
ElevenLabs’ Vision for Voice Interfaces | CEO Mati Staniszewski
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 fil
95% Faster Video Production with Synthesia | Victor Riparbelli
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:
From Idea To Impact: How Gamma Is Redefining Presentations | Grant Lee
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
Leadership Lessons From Snowflake’s Sales & Marketing Duo | Chris Degnan and Denise Persson
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, Mak
The Man Who Builds for the Decade Ahead | Founder of Google X, Waymo, and Udacity
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 hist
How WordPress Became a Web Giant | Automattic Founder and CEO Matt Mullenweg
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
The Central Nervous System for Modern Business | Confluent CEO Jay Kreps
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
Airtable’s AI Reboot with CEO Howie Liu
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 AirtableChapters:00:00 Intro01:04 First startup & YC04:06 Salesforce acqui-hire07:31 Li
Inside the Mind of the World’s Most Optimistic CEO
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:Why Bill bought a deli when he was in high school — and how he competed against 7-Elev
How Dropbox Beat Big Tech in the Cloud Wars
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,
Building High-Impact Sales Teams | Dan Lee and Nooks
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-foun
Shishir Mehrotra on Building Tools Creators Love
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,
How Notion Reimagined Productivity Tools | Ivan Zhao
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 NotionMentioned in this episode: Fuzzy Khosrowshahi, Airbnb, Se
The Travel Giant Built on Billions of Reviews | Steve Kaufer on TripAdvisor
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, smar
The Expert Network Behind Handshake AI’s Model Training w/ Garrett Lord & Mamoon Hamid
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 l
How Plaid Turned a Failed $5.3B Deal with Visa into Momentum | Zach Perret (Plaid)
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 c
Episode 250: AI Special Featuring Sierra, Harvey, Windsurf & More
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 CE
How Imprint Is Reinventing Credit Cards for Modern Brands | Daragh Murphy
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: Darag
GitLab’s CEO on Why the Next Great Developer Might Not Write Code | Bill Staples
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 engi
Stord’s Plan to Take on Amazon’s Logistics Advantage | Sean Henry
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, mid
Family, Focus, and 350M Users: Inside Zoom with Eric Yuan
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
Bret Taylor’s Journey Leading Salesforce, Sierra & OpenAI
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 oft
Inside Aurora’s Push to Make Autonomous Trucking Real | Chris Urmson
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 a
From Scaling Cisco to Seeding AI: John T. Chambers on Speed, Strategy, and Reinvention
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 ho
How Matt Murphy Made Marvell Essential to AI and Cloud
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 les
HubSpot CEO on the Future of SaaS, AI, & Leading Through Change
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, h
From White House to Wall Street: David Rubenstein
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
No Reset Button: Reinventing Amplitude in a Post-AI World (Spenser Skates)
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 edg
Flexport’s Third Act: Winning in a Broken Global Trade System
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 $
Brex 3.0: Inside the Radical Turnaround with Pedro Franceschi
Guest: Pedro FranceschiPedro 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
From India to Silicon Valley: The Jay Chaudhry & Zscaler Story
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 d
The Unlikely Path to Building a Billion-Dollar Gov Tech Company | Zac Bookman
Guest: Zac Bookman, CEO and Co-Founder of OpenGovThirteen 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 believe
Bootstrapped to $12B: Mailchimp’s Ben Chestnut on Life After the Exit
Guest: Ben Chestnut, Former CEO and Co-Founder of MailchimpIf 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 esti
Meet the Man Who’s Making Supersonic Flight Possible Again | Blake Scholl
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
#232 CEO NetApp, George Kurian: New Chapters
Guest: George Kurian, CEO of NetAppFor 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 produc
#231 CEO & Co-Founder Harvey, Winston Weinberg w/ Ilya Fushman: Worthy Sacrifices
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
#230 Co-founder & CEO, Wolt & Head of DoorDash International, Miki Kuusi: The Next Mountain
Guest: Miki Kuusi, head of international at Doordash + CEO & co-founder of Wolt + co-founder of Slush tech conferenceBefore 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 a
#229 Former CEO Activision Blizzard, Bobby Kotick w/ Bing Gordon: Change the Game
Guest: Bobby Kotick, former CEO of Activision Blizzard; and Bing Gordon, Advisor at Kleiner PerkinsIn 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 b
#228 Co-Founder Alinea & Tock: Selling Experience
Guest: Nick Kokonas, co-founder of the Alinea Group and former CEO of TockAs 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 th
#227: CEO & Founder Axon, Rick Smith: Push Risk
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
#226 President & COO Coinbase, Emilie Choi: Through the Storm
Guest: Emilie Choi, president & COO of CoinbaseAfter 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
#225 CEO Lattice, Sarah Franklin: Trailblazer
Guest: Sarah Franklin, CEO of LatticeAs 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 d
#224 CTO & Co-Owner 37signals, David Heinemeier Hansson: Perfect Flow
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
#223 Great Stories and Gritty Advice for 2025
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 & runni
#222 CEO San Francisco Giants, Larry Baer: Winning Plays
Guest: Larry Baer, CEO of the San Francisco GiantsIn 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 financ
#221 CEO & Chairman Sony Pictures, Tony Vinciquerra: Into the Fire
Guest: Tony Vinciquerra, outgoing CEO of Sony PicturesTony 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
#220 Former CEO Amazon Worldwide Consumer, Jeff Wilke: Exponential
Guest: Jeff Wilke, former CEO of Amazon Worldwide Consumer and chairman of Re:Build ManufacturingJeff 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 runnin
#219 CEO Tanium, Dan Streetman: Critical Responsibility
Guest: Dan Streetman, CEO of TaniumA 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,
#218 CEO Etsy, Josh Silverman: Second Acts
Guest: Josh Silverman, CEO of EtsyWhen 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 vi
#217 CEO & Co-Founder Codeium, Varun Mohan w/ Leigh Marie Braswell: Limitless
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
#216 Founder Khan Academy, Sal Khan: Dangerously Curious
Guest: Sal Khan, founder of Khan AcademyAI 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 re
#215 COO Rippling Matt MacInnis: Learn the Engine
Guest: Matt MacInnis, COO of RipplingOne 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
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