Grit

PODCAST · business

Grit

Grit explores what it takes to create, build, and scale world-class organizations. It features weekly episodes highlighting the leaders who are pushing their companies to make a difference. This series is hosted by Joubin Mirzadegan, go to market operating partner at Kleiner Perkins, a venture capital firm investing in history-making founders.

  1. 285

    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 ZaffinoConnect with Peter ZaffinoLinkedInConnect with Joubin:XLinkedInEmail: [email protected] on LinkedInFollow on X​Learn more about Kleiner Perkins

  2. 284

    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 SaarinenXLinkedInConnect with Josh Coyne:XLinkedInConnect with Joubin:XLinkedInEmail: [email protected] on LinkedInFollow on X​Learn more about Kleiner Perkins

  3. 283

    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 ultimately compounds into market leadership.Guest: Kevin Mandia, Founder and CEO, ArmadinConnect with Kevin MandiaLinkedIn: https://www.linkedin.com/in/kevin-mandia-0a07173/Connect with Josh Coyne:XLinkedInConnect with Joubin:XLinkedInEmail: [email protected] on LinkedInFollow on X​Learn more about Kleiner Perkins

  4. 282

    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 called the "Department of War" again.Guest: Emil Michael, U.S. Under Secretary of Defense for Research and EngineeringConnect with Emil MichaelXLinkedInConnect with JoubinXLinkedInEmail: [email protected] on LinkedIn:https://www.linkedin.com/company/kpgritFollow on X:https://x.com/KPGrit​Learn more about Kleiner Perkins

  5. 281

    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 where people stop working.Guest: Bret Taylor, co-founder of SierraConnect with Bret XLinkedInConnect with JoubinXLinkedInEmail: [email protected] GritLinkedInX​Learn more about Kleiner Perkins:https://www.kleinerperkins.com/

  6. 280

    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 next wave of threats, which are plentiful?”Guest: Marcin Kleczynski, CEO at MalwarebytesConnect with Marcin KleczynskiX: https://x.com/mkleczynskiLinkedIn: https://www.linkedin.com/in/marcinkleczynski/Connect with JoubinX: https://x.com/JoubinmirLinkedIn: https://www.linkedin.com/in/joubin-mirzadegan-66186854/Email: [email protected] on LinkedIn:https://www.linkedin.com/company/kpgritFollow on X:https://x.com/KPGrit​Learn more about Kleiner Perkins: https://www.kleinerperkins.com/

  7. 279

    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 customer demographics.Guest: Ping Wu, CEO of CrestaConnect with Ping WuX: https://x.com/ping_wuLinkedIn: https://www.linkedin.com/in/pingwu/Connect with JoubinX: https://x.com/JoubinmirLinkedIn: https://www.linkedin.com/in/joubin-mirzadegan-66186854/Email: [email protected] on LinkedIn:https://www.linkedin.com/company/kpgritFollow on X:https://x.com/KPGrit​Learn more about Kleiner Perkins: https://www.kleinerperkins.com/ 

  8. 278

    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, Chairman and CEO at Circle​Connect with Jeremy AllaireX: https://x.com/jerallaireLinkedIn: https://www.linkedin.com/in/jeremyallaire/Connect with JoubinX: https://x.com/JoubinmirLinkedIn: https://www.linkedin.com/in/joubin-mirzadegan-66186854/Email: [email protected] on LinkedIn:https://www.linkedin.com/company/kpgritFollow on X:https://x.com/KPGrit​Learn more about Kleiner Perkins:https://www.kleinerperkins.com/ 

  9. 277

    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.”“I have no doubts that AI capabilities are just going to increase more and more over the next few years. But even more important is this concept of how much are we even leveraging what AI can do today? I would say that we've not even used 1% of current capabilities of these models”“If you're trying to be everything to everyone, then you just cannot compete with somebody who's focused on a smaller problem and going deep into that.”You can also listen to Arvind’s earlier episode here: https://www.youtube.com/watch?v=iIH0Qp6d6bg&list=PLRiWZFltuYPF8A6UGm74K2q29UwU-Kk9k&index=96Guest: Arvind Jain, founder and CEO, Glean​Connect with Arvind JainX: https://x.com/jainarvindLinkedIn: https://www.linkedin.com/in/jain-arvind/Connect with JoubinX: https://x.com/JoubinmirLinkedIn: https://www.linkedin.com/in/joubin-mirzadegan-66186854/Email: [email protected] on LinkedIn:https://www.linkedin.com/company/kpgritFollow on X:https://x.com/KPGrit​Learn more about Kleiner Perkins:https://www.kleinerperkins.com/

  10. 276

    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 (co-founder of Cloudflare) Evan Spiegel (co-founder and CEO of Snap) Connect with JoubinX: https://x.com/JoubinmirLinkedIn: https://www.linkedin.com/in/joubin-mirzadegan-66186854/Email: [email protected] on LinkedIn:https://www.linkedin.com/company/kpgritFollow on X:https://x.com/KPGrit​Learn more about Kleiner Perkins: https://www.kleinerperkins.com/

  11. 275

    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 timelines.Guest: James Cadwallader, co-founder and CEO of Profound and Ilya Fushman, partner at Kleiner PerkinsConnect with James CadwalladerX: https://x.com/thejamescad?lang=enLinkedIn: https://www.linkedin.com/in/jsca/​Connect with Ilya FushmanX: https://x.com/ilyafLinkedIn: https://www.linkedin.com/in/ilyafushman/Connect with JoubinX: https://x.com/JoubinmirLinkedIn: https://www.linkedin.com/in/joubin-mirzadegan-66186854/Email: [email protected] on LinkedIn:https://www.linkedin.com/company/kpgritFollow on X:https://x.com/KPGrit​Learn more about Kleiner Perkins: https://www.kleinerperkins.com/

  12. 274

    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 Inc. and Bing Gordon, Advisor at Kleiner Perkins​Connect with Evan SpiegelX:https://x.com/evanspiegel?lang=enLinkedIn:https://www.linkedin.com/in/evan-spiegel/​Connect with Bing GordonX: https://x.com/bingfish LinkedIn: https://www.linkedin.com/in/binggordon/Connect with JoubinX: https://x.com/JoubinmirLinkedIn: https://www.linkedin.com/in/joubin-mirzadegan-66186854/Email: [email protected]​Learn more about Kleiner Perkins:https://www.kleinerperkins.com/ 

  13. 273

    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 with enterprise revenue leaders.Stepping into the host role, Mamoon Hamid joins Joubin to talk about his transition from sales leader to founder, how Roadrunner came together, and why it became our first incubation since Glean.Roadrunner is hiring! Check them out: https://www.roadrunner.ai/Guest: Joubin Mirzadegan, Partner, Kleiner Perkins​Connect with MamoonXLinkedInConnect with JoubinXLinkedInEmail: [email protected]​Learn more about Kleiner Perkins

  14. 272

    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 creators regain control in an AI driven internet.Guest: Michelle Zatlyn, co-founder and President of CloudflareConnect with Michelle ZatlynXLinkedIn​Connect with JoubinXLinkedInEmail: [email protected]​Learn more about Kleiner Perkins

  15. 271

    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 BoardConnect with Brynn PutnamXLinkedInConnect with JoubinXLinkedInEmail: [email protected]​Learn more about Kleiner Perkins

  16. 270

    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 how the race among AI labs is really unfolding.Guest: Aidan Gomez, co-founder and CEO of CohereConnect with Aidan: XLinkedInConnect with Joubin: XLinkedInEmail: [email protected] more about Kleiner Perkins

  17. 269

    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 for Wall Street.Guest: Howard Lerman, co-founder and former CEO of Yext, and founder and CEO of Roam​Connect with Howard LermanXLinkedInConnect with JoubinXLinkedInEmail: [email protected]​Learn more about Kleiner Perkins

  18. 268

    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 decisions that give you energy.”Guest: Dan O’Connell, CEO of Front​Connect with Dan O’ConnellXLinkedIn​Connect with JoubinXLinkedInEmail: [email protected]​Learn more about Kleiner Perkins

  19. 267

    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 filmmaking.Guest: Mati Staniszewski, co-founder and CEO of ElevenLabsConnect with Mati StaniszewskiXLinkedIn​Connect with JoubinXLinkedInEmail: [email protected]​​Learn more about Kleiner Perkins

  20. 266

    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: Victor Riparbelli, CEO and co-founder of Synthesia and Josh Coyne, Partner at Kleiner PerkinsConnect with Victor RiparbelliX: https://x.com/vriparbelliLinkedIn: https://www.linkedin.com/in/victorriparbelli/​Connect with Josh CoyneX: https://x.com/josh_coyneLinkedIn: https://www.linkedin.com/in/joshuacoyne/​Connect with JoubinX: https://x.com/JoubinmirLinkedIn: https://www.linkedin.com/in/joubin-mirzadegan-66186854/Email: [email protected]​Learn more about Kleiner Perkins:https://www.kleinerperkins.com/

  21. 265

    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 LeeXLinkedInConnect with JoubinXLinkedInEmail: [email protected] more about Kleiner Perkins

  22. 264

    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, 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 Snowflake.Connect with Chris Degnan LinkedIn​Connect with Denise PerssonLinkedIn​Connect with JoubinXLinkedInEmail: [email protected]​Learn more about Kleiner Perkins:https://www.kleinerperkins.com/

  23. 263

    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 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 UdacityConnect with Sebastian ThrunXLinkedIn​Connect with JoubinXLinkedInEmail: [email protected]​Learn more about Kleiner Perkins

  24. 262

    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 democratize publishing and commerce through paid sabbaticals and remote work.Guest: Matt Mullenweg, co-founder of WordPress and founder and CEO of AutomatticConnect with Matt MullenwegXLinkedInConnect with JoubinXLinkedInEmail: [email protected]​Learn more about Kleiner Perkins

  25. 261

    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 longer than most people expect.​Guest: Jay Kreps, Co-Founder & CEO of ConfluentConnect with JayXLinkedInConnect with JoubinXLinkedInEmail: [email protected]​Learn more about Kleiner Perkins

  26. 260

    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 Life-changing exit at 2211:07 Scaling too fast, layoffs14:04 Sparks vs. coasting growth19:33 Two years to launch24:04 Could AI Build It Faster?27:06 Vibe coding & AI startups36:47 Everyone can build software41:08 Refounding Airtable with AI51:04 Sprint vs. marathon58:15 Cap tables & control01:03:29 Always be hiring01:05:00 What grit meansLinks:Connect with HowieXLinkedInConnect with AirtableWebsite: airtable.comXLinkedInConnect with JoubinXLinkedInEmail: [email protected] more about Kleiner Perkins

  27. 259

    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-Eleven (04:00)Interviewing at Xerox and wanting it more than anyone else (08:17)Unwavering optimism and being a source of strength for others (12:34)How a love of work has shaped Bill as a person (16:44)Facing challenges and keeping a promise to his father (22:00)Enjoying the present and keeping an eye on the future (30:01)Leaving Xerox for Gartner and learning from a tough experience (33:29)Sloan Kettering and Father Michael Judge (39:22)Following the “original dream” vs. building something new at ServiceNow (44:59)Losing an eye and getting a pep talk from two Medal of Honor winners (51:15)Why Bill started and ended his book with quotes from two Kennedys (01:01:21)Connect with BillXLinkedInConnect with JoubinXLinkedInEmail: [email protected] Learn more about Kleiner Perkins

  28. 258

    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, Co-Founder & CEO of DropboxChapters:00:00 Trailer00:52 Introduction01:35 Towards full autonomy16:20 Coming back to school21:45 Golden ticket to California25:23 No one’s born a CEO28:15 Y Combinator and a co-founder37:53 The craft of being a great CEO53:41 Metabolizing the stress1:10:14 Tactical advices and frameworks1:27:48 Who Dropbox is hiring1:29:35 What “grit” means to Drew1:32:10 OutroLinks:Connect with DrewXLinkedInConnect with JoubinXLinkedInEmail: [email protected] more about Kleiner Perkins

  29. 257

    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-founder of Nooks and Leigh Marie Braswell, Partner at Kleiner PerkinsConnect with Dan Lee: XLinkedInConnect with Leigh Marie BraswellXLinkedInConnect with JoubinXLinkedInEmail: [email protected] more about Kleiner Perkins

  30. 256

    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, beginning with Superhuman’s email experience.Guest: Shishir Mehrotra, co-founder of Coda and CEO of GrammarlyConnect with ShishirXLinkedInChapters: 00:00 Trailer01:24 Introduction02:09 Zoo vs safari12:02 A TV ahead of its time21:25 Product decisions31:25 The data behind the algorithm37:26 The AI native productivity suite48:06 Agents are digital humans57:55 Pressure trade-off1:12:50 Insulated from judgment1:25:19 Who Grammarly is hiring1:25:51 What “grit” means to Shishir1:29:30 OutroMentioned in this episode: YouTube, Ray William Johnson, Spotify, Twitch, MTV, Chris Cox, Facebook, TikTok, Google TV, Centrata, Google Chrome, Android, Gmail, Microsoft, Super Bowl, Mosaic, Panasonic, Sony, Susan Wojcicki, Rishi Chandra, Apple TV, Amazon Firestick, Comcast, LoudCloud (Opsware), Quest Communications, AT&T Southwestern Bell, Salar Kamangar, Patrick Pichette, Eric Schmidt, OpenAI ChatGPT, Google Gemini, Mark Zuckerberg, Meta Platforms, Sundar Pichai, Larry Page, Sergey Brin, Hamilton, Reid Hoffman, Sam Altman, Tesla, Waymo, Airtable, Notion, Max Lytvyn, Alex Shevchenko, Superhuman, Duolingo, Luis von Ahn, Khan Academy, MrBeast, Facebook Messenger, Snap (Snapchat), WhatsApp, Google+, Meta LLaMa, Satya Nadella, Tim Cook, Daniel GrossConnect with JoubinXLinkedInEmail: [email protected] more about Kleiner Perkins

  31. 255

    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, Sequoia Capital, Linear, Figma, Apple, Things, Microsoft, BMW, Lumiere, The Beatles, The Rolling Stones, Eric Clapton, Rippling, Matt MacInnis, Inkling, Steve Jobs, Douglas Engelbart, Alan Kay, Bill Gates, OpenAI ChatGPT, Y Combinator, Andrej Karpathy, Toby Schachman, Simon Last, Spotify, SlackConnect with Ivan ZhaoXLinkedInConnect with JoubinXLinkedInEmail: [email protected] more about Kleiner Perkins

  32. 254

    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, smarter, and at scale.Guest: Steve Kaufer, co-founder of TripAdvisorChapters:(00:00) Trailer(00:45) Introduction(01:32) Early days of Tripadvisor(08:14) Catching the startup bug(18:42) Luck and timing(26:54) $200M: a combo of money and risk(37:37) I love creating stuff(40:45) Hardest part of being a public CEO(46:21) Never let a good crisis go to waste(51:54) An average traveler(55:49) Social proof vs artificial intelligence(1:02:59) Back in the saddle(1:09:54) Not for the faint of heart(1:12:16) What “grit” means to Steve(1:12:31) OutroMentioned in this episode: Google, Expedia Group, Barry Diller, Interactive Corporation (IAC), Uber, Dara Khosrowshahi, OpenAI ChatGPT, IMDb, CJ Affiliate (Commission Junction), Amazon, Google Chrome, Give Freely, Honey, Rakuten, Macy’s, American Cancer Society, Google GeminiLinks:Connect with SteveXLinkedInConnect with JoubinXLinkedInEmail: [email protected] more about Kleiner Perkins

  33. 253

    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 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.Connect with Garrett LordXLinkedInConnect with JoubinXLinkedInEmailConnect with MamoonXLinkedInLearn more about Kleiner Perkins

  34. 252

    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 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 with ZachXLinkedInConnect with JoubinXLinkedInEmail: [email protected] more about Kleiner Perkins

  35. 251

    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 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://x.com/Joubinmir Email: [email protected] more about Kleiner Perkins: https://www.kleinerperkins.com

  36. 250

    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: Daragh Murphy, CEO & Co-Founder of ImprintChapters:00:00 Trailer00:48 Introduction01:30 Actualizing the dream08:37 Imprint11:37 Partnerships are massive16:48 Understand the market18:42 “Get more, spend more” tradeoffs23:57 Fishing in the wrong ponds31:32 Can’t skip work32:43 Exciting and scary34:56 Pride and ownership46:50 The way you spend your day50:20 New technologies54:51 Who Imprint is hiring54:59 What “grit” means to Daragh55:34 OutroMentioned in this episode: Figma, Rippling, H-E-B Grocery Company, LP, Barclays US, IBM, Coinbase, Charlie Munger, Instagram, Hamptons, Google, Nick Huber, Ribbit, Ireland, WeWork, Adam Kim, Amazon, Shopify, Tobias Lütke, Duolingo, Parker ConradLinks:Connect with DaraghLinkedInConnect with JoubinXLinkedInEmail: [email protected] more about Kleiner Perkins

  37. 249

    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 engineers by auto-debugging code and closing security gaps.Guest: Bill Staples, CEO of GitLabChapters:00:00 Trailer00:42 Introduction02:34 True joy in life08:16 Winning teams13:53 When the energy isn’t there18:00 Super ambitious21:01 It’s not just technology29:27 Elevating quality and standard41:36 Lifelong collaborator51:22 Competent intelligence54:22 Structuring goals and time1:03:59 Who GitLab is hiring1:04:17 What “grit” means to Bill1:04:54 OutroLinks:Connect with BillLinkedInConnect with JoubinXLinkedInEmail: [email protected] more about Kleiner Perkins

  38. 248

    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, 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 StordLinks:Connect with Sean HenryXLinkedInConnect with JoubinXLinkedInEmail: [email protected] more about Kleiner Perkins

  39. 247

    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 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 of AI startups.Guest: Eric S. Yuan, Founder & CEO of ZoomChapters: 00:00 Trailer00:44 Introduction01:47 Walking with swagger03:48 Extremely exciting moment10:05 Classic innovators’ dilemma12:59 Laser-focused bandwidth17:56 Family first: lead by example22:09 Everybody was doing their road shows25:34 The entire world was dependent28:04 Community care31:57 Valuation and a co-founder35:17 A lot of unhappy days39:25 Building Zoom for consumers46:57 Holograms?52:01 Home53:23 Huge competition, high velocity1:00:33 Where companies get wrong1:04:52 Giving back1:13:12 Who Zoom is hiring1:13:24 What “grit” means to Eric1:14:24 OutroMentioned in this episode: Webex by Cisco, Glean, Apple, HP, Netscape, Yahoo, Brian Armstrong, Emilie Choi, Coinbase, New Limit, Elon Musk, Windy Hill, Magic Leap, Rony Abovitz, Jony Ive, OpenAI ChatGPT, Bill McDermott, ServiceNow, Carl EschenbachLinks:Connect with EricXLinkedInConnect with JoubinXLinkedInEmail: [email protected] more about Kleiner Perkins

  40. 246

    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 often come from everyday friction, and how staying relentlessly focused can unlock real momentum in AI.Guest: Bret Taylor, Co-Founder of SierraChapters:00:00 Trailer00:49 Introduction01:57 Saving OpenAI09:15 Overwhelming yet capable of a lot13:36 Father and founder16:49 History is written by the victors22:13 How you price matters35:58 Stickiest piece of software49:48 The first realtime social network55:34 Facebook CTO who rewrote Google Maps1:02:10 Least known, most impressive1:11:39 The best way to predict the future1:16:22 Most personally passionate1:21:22 Currency of reputation1:27:17 Away from work1:28:35 Who Sierra is hiring1:28:58 What “grit” means to Bret1:29:18 OutroMentioned in this episode: Google Maps, Salesforce, OpenAI ChatGPT, Meta Facebook, X (formerly Twitter), Sam Altman, Elon Musk, Mark Zuckerberg, Google, Marissa Mayer, Excite, MSN, AltaVista, Amazon, Harvey, Airbnb, Coinbase, Apple, John Doerr, Cursor, Codeium Windsurf, Perplexity, xAI, Kleenex, Amazon Web Services (AWS), FriendFeed, Tumblr, Kevin Gibbs, Google Maps, Yelp, Trulia, iOS App Store, Blackberry, Facebook Messenger, Marvel Avengers, Slack, Quip, Leonardo da Vinci, Clay Bavor, Microsoft, Eric Schmidt, Alan Kay, Brian Armstrong, Brian Chesky, Shopify, SiriusXM, Patrick CollisonLinks:Connect with Bret TaylorXLinkedInConnect with JoubinXLinkedInEmail: [email protected] more about Kleiner Perkins

  41. 245

    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 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 eight years into Aurora, Urmson says the future he’s been chasing is finally within reach.Guest: Chris Urmson, Co-Founder & CEO of AuroraChapters: 00:00 Trailer00:43 Introduction01:59 FSD: are we there? 14:31 The competition, a million dollar check from LA to LV22:50 Dream like an amateur, execute like a pro32:30 Operate with integrity42:49 The future is here, unevenly distributed49:36 Underestimated decisions, minimizing regrets1:03:55 Retaining value1:16:45 Integrating self-driving1:28:20 Lifer1:29:25 Who Aurora is hiring1:29:53 What “grit” means to Chris1:30:15 OutroMentioned in this episode: Waymo, Google, Rivian, Dmitri Dolgov, Uber, Tesla, The DARPA Grand Challenge, Defense Advanced Research Projects Agency, United States Department of Defense, Carnegie Mellon University, Stanford University, FedEx, Werner Enterprises, Hirschbach, Schneider Electric, Larry Page, Sergey Brin, Sebastian Thrun, Batman, Kentucky Fried Chicken, Anthony Levandowski, Donald Trump, Apple iPhone, Airbnb, Blackmore, Stripe, Titan, Ford, Volkswagen, RJ Scaringe, Peterbilt Motors Company, The Volvo Group, Continental AG, Dara KhosrowshahiLinks:Connect with Chris UrmsonXLinkedInConnect with JoubinXLinkedInEmail: [email protected] Learn more about Kleiner Perkins

  42. 244

    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 how he’s backing the next generation of AI-native startups.Guest: John T. Chambers, Former Cisco Executive Chairman & CEO, JC2 Ventures Founder & CEOChapters: 00:00 Trailer00:45 Introduction01:45 Track record, relationships, trust13:21 Acquisitions every year17:32 Product-focused24:40 Family, dyslexia, and without shame30:46 Wang Laboratories35:59 Ready being CEO40:17 Reinventing your business50:08 Numbers don’t lie54:09 Sales calls and making mistakes56:20 Adapting leadership style1:06:32 Best leadership year ever1:13:35 A busy, exhausting schedule1:22:07 Candid with me1:25:21 What “grit” means to John1:26:43 OutroMentioned in this episode: John Doerr, OpenAI, Wang Laboratories, IBM, Microsoft, Google, Amazon, Apple Inc., Meta Platforms, FMC Corporation, DuPont de Nemours, Inc., John Mortgage, Don Valentine, Sequoia Capital, Alcatel Mobile, Lucent Technologies, Inc., Verizon Communications Inc., AT&T Inc., Rick Justice, Pankage Patel, Larry Carter, CNBC, Jim Cramer, George Kurtz, CrowdStrike, Randy Pond, Rebecca Jacoby, Mel SelcherLinks:Connect with JohnXLinkedInConnect with JoubinXLinkedInEmail: [email protected] more about Kleiner Perkins

  43. 243

    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 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 Trailer00:47 Introduction03:00 Huge company, taking the long view10:28 Market cap shift to big tech14:44 The data infrastructure opportunity20:30 Massive economic opportunity31:33 Semiconductor industry and geopolitics40:46 Taiwan and Moore’s Law 44:05 Getting hammered down 50%47:05 Silicon Valley51:15 All in despite risks55:37 The CEO checkbox1:01:22 Email from Matt, subject: Grit1:07:35 The higher you go1:15:44 Who Marvell is hiring1:20:14 What “grit” means to Matt1:24:40 OutroMentioned in this episode: Jim Cramer, Taiwan Semiconductor Manufacturing Company Limited (TSMC), Maxim Integrated, Mattel, Inc., Cisco Systems, Inc, Juniper Networks, Meta Platforms, Amazon.com, Inc., Cavium, Inc., Inphi Corporation, Aquantia Corporation, Mellanox Technologies, Nvidia Corporation, Microsoft Corporation, OpenAI, Anthropic, John Chambers, Facebook, Spotify, Airbnb, Google, Barack Obama, Ronald Reagan, Donald Trump, Intel Corporation, Robert Norton Noyce, Gordon Moore, Advanced Micro Devices, Inc. (AMD), Andrew "Andy" Stephen Grove, Bloomberg, Intuit Inc., Lip-Bu Tan, Sehat Sutardja, Whay S. Lee, Starboard Value, Rick Hill, Novellus Systems, Inc., Michael Strachan, Deloitte & Touche LLP, Apple Inc., Steve Jobs, Chris KoopmansLinks:Connect with MattLinkedInConnect with JoubinXLinkedInEmail: [email protected] more about Kleiner Perkins

  44. 242

    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, her take on why data is the new battleground in tech.Chapters: 00:00 Trailer00:52 Introduction02:22 Fire in my belly10:06 Constraints12:19 Peak performance16:38 Helping while in sheer panic21:43 The general ethos30:14 Customer value36:08 Excited and scared47:25 Becoming CEO54:19 Feeling behind1:01:51 Very lonely1:05:34 Losing credibility1:08:42 Slowing down, sitting still1:12:31 No patience to finish a book1:15:39 Who HubSpot is hiring1:15:54 What “grit” means to Yamini1:16:45 OutroMentioned in this episode: Sequoia Capital, Carl Pieri, Brian Halligan, Zoom Workplace, Meta Platforms, Google, Anthropic, Microsoft, Salesforce, Blockbuster Video, BlackBerry Limited, Axon Enterprise, Netflix, Snapchat, Harvey, Dharmesh Shah, Gödel, Escher, Bach: an Eternal Golden Braid, Sapiens: A Brief History of HumankindLinks:Connect with YaminiXLinkedInConnect with JoubinXLinkedInEmail: [email protected] more about Kleiner Perkins

  45. 241

    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 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 Trailer00:53 Introduction01:40 Family, wealth, class14:40 Happiness disparity and longevity19:25 I need more to give away more25:04 The relentless fundraiser 33:53 Kids and travel36:06 No track record, the great white buffalo38:59 Business and politics43:53 Fired from Washington45:52 Fundraising, presidents, podcast guests48:04 Private equity and sports53:44 Expenses — no charges55:49 Waking up with energy 57:26 Preserving copies1:02:05 Organizational architecture1:03:41 Bury me in my plane1:08:11 Not a big luxury spender1:10:32 What “grit” means to David1:10:50 OutroMentioned in this episode: Andrew Rubenstein, Stanford University, Bill Gates, Melinda Gates, Warren Buffett, Morgan Guaranty Trust Company, International Business Machines Corporation (IBM), Procter & Gamble Company, Forbes 400, Duke University, University of Chicago, Harvard Corporation, Johns Hopkins University, California Public Employees' Retirement System (CalPERS), President of the United States of America, Donald J. Trump, Jimmy Carter, John F. Kennedy Center for the Performing Arts, Smithsonian Institution, National Gallery of Art, George W. Bush, Barack Obama, Joe Biden, Arianna Huffington, Xi Jinping, Hank Greenberg, Stephen A. Schwarzman, Tim Cook, Jeff Bezos, Baltimore Orioles, Fred Trammell Crow, Harlan Crow, National Basketball Association (NBA), National Football League (NFL), Arctos Partners LP, Anthropic, Magna Carta Libertatum, Declaration of Independence, Emancipation Proclamation, Abraham Lincoln, US Constitution, National Archives, Lincoln Memorial, Thomas Jefferson Memorial, Mount Vernon, Monticello, Montpelier, Mark Cuban, Paul McCartneyConnect with David:X: @DM_RubensteinConnect with Joubin:X: @JoubinmirLinkedIn: Joubin MirzadeganEmail: [email protected]

  46. 240

    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 edge—and why taking the company public early was a risk worth taking. Chapters:00:00 Trailer00:43 Introduction01:26 AI is still very early05:48 The urgency of building from the ground up08:49 Bringing in new blood11:23 Higher valuations and going public15:00 Who’s leading who18:39 Markets being open and closed21:14 Being the incumbent in AI24:40 Slow innovation31:43 The ultimate founder37:06 Things willing to relinquish44:04 Being the person I want to be46:41 Between family and work50:08 Becoming the person you hate55:16 Chief general, chief justice, chief priest1:02:56 Tired founders1:04:32 Missing out1:14:51 Who Amplitude is hiring1:15:41 What Spenser means to Spenser1:16:54 OutroMentioned in this episode: OpenAI ChatGPT, Command AI, Oracle Corporation, Anthropic Claude, Jeff Bezos, Steve Jobs, Bill Gates, Larry Ellison, Rippling, Stripe, Meta Platforms, Inc., Mark Zuckerberg, Figma, Canva, Peter Thiel, Anne Lee Skates, Ruth Bader Ginsburg, Michael JordanLinks:Connect with SpenserXLinkedInConnect with JoubinXLinkedInEmail: [email protected] more about Kleiner Perkins

  47. 239

    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 $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 trade.Chapters: 00:00 Trailer00:31 Introduction02:07 Meeting smart people, seeing the world03:40 Eroded margins09:52 Charismatic and overconfident15:32 Not an overnight decision20:08 The founder has returned23:10 Redoing the hiring26:38 No substitute for passion31:00 Working for and with my brother37:28 Working with forwarders42:14 Being a founder can be lonely47:49 Life’s work54:06 The right person for the job1:00:55 19 countries1:04:57 Blowing people up1:07:24 Work and being a good dad1:08:34 Not doing it for money and loving money1:17:52 Import and export tariffs1:22:57 De minimis1:25:54 Panama and the Suez Canal1:36:50 Going public1:42:24 Who Flexport is Hiring 1:42:42 What "grit" means to Ryan1:43:06 OutroMentioned in this episode: Founders Fund, Amazon, Toyota Motor Corporation, Slack, Brex, Pedro Franceschi, Henrique Dubugras, United States Customs and Border Protection, ImportGenius, Michael Kanko, Y Combinator, Paul Graham, Intel Corporation, Shopify, Geely Holding (Zhejiang Geely Holding Group Co., Ltd.), The Volvo Group, Intuit TurboTax, David Petersen, BuildZoom, TechCrunch, Google, Figma, Barack Obama, Donald Trump, Jimmy Carter, Panama Canal Authority, United States Navy, Coinbase, Uber, AirbnbLinks:Connect with RyanXLinkedInConnect with JoubinTwitterLinkedInEmail: [email protected] more about Kleiner Perkins

  48. 238

    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 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 Trailer00:46 Introduction01:45 Startup roller coaster05:21 Founders know how to have fun07:12 Belief barrier evolution12:00 Early state of life in Brazil13:23 Controlling variables15:32 Screen time19:23 Making small decisions23:27 Learning raises the bar26:15 People manager38:49 Getting underwater42:05 Growth accelerated47:51 Vision from the top down52:13 Leadership organization54:01 AI software engineering physics54:43 People complain about change59:42 Believers and non-believers1:04:09 Equity and bonus controversy1:08:40 Big swings and going public1:14:15 Control in unpredictability1:18:04 Living in a pixel1:19:52 Meditate, sleep, diet, exercise1:24:36 Mental health and stress1:33:12 Who Brex is hiring1:33:49 What "grit" means to Pedro1:34:39 OutroMentioned in this episode: Silicon Valley, Facebook, Meta Platforms, Inc., Mark Zuckerberg, Mastercard, Rio de Janeiro, iPhone, Bill Gates, Tim Urban, Jony Ive, Apple Inc., LinkedIn, Salesforce, Brian Chesky, Airbnb, Anthropic Claude, Cursor, Codeium Windsurf, Cognition Labs Devin, Vercel, Retool AI, Amplitude, Spenser Skates, Elon Musk, Tesla, Inc.Links:Connect with Pedro:XLinkedInConnect with Joubin:XLinkedInEmail: [email protected] episode was produced by Kleiner Perkins and edited by IQvideo.The trailer and distribution for this episode were handled by Atomik Growth.Learn more about Kleiner Perkins

  49. 237

    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 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.Chapters:00:00 Trailer00:42 Introduction01:21 His fifth company04:26 Entrepreneurs’ existential fear10:53 Customer engagement and new innovations12:46 No private jets, no business class19:34 “I never used money”23:38 Born and raised in India26:17 Hiring legends30:35 Walking on water35:09 “Dolphining”39:55 Areas of weakness42:11 Passionate even on the weekends44:56 Work during roller coasters47:35 The weight of the world is on your shoulders49:21 Leveraging AI56:20 OutroMentioned in this episode: Elon Musk, Microsoft, Bill Gates, BlackBerry, Steve Ballmer, Satya Nadella, Hewlett-Packard (HP), IBM, John Fellows Akers, Steve Jobs, NeXT, Inc., Linux, Cisco, United Airlines, San Francisco International Airport, Sundar Pichai, Ravi Mhatre, Lightspeed Venture Partners, Six Flags, AI (artificial intelligence), securityLinks:Connect with JayLinkedInConnect with JoubinXLinkedInEmail: [email protected] Learn more about Kleiner Perkins

  50. 236

    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 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 sell. “These people buy and don't sell,” Zac said of Cox. “They're all in on the mission. And they're all in on taking care of employees. So I see a triple win: A win for employees, win for the investors, win for the customers, maybe a quadruple win for me and the management.”Chapters:(01:46) - OpenGov’s mission (04:34) - Shrinking the product-market fit (07:34) - Super misson driven (08:59) - Why OpenGov almost shut down (13:08) - Zac’s early career (16:16) - Picking (and losing) a CTO (22:50) - Growing upside-down (25:29) - The SPAC backstabber (31:26) - Why Zac didn’t get fired (33:24) - Selling in 2024 (37:04) - Growth by acquisition (42:31) - John Chambers and PMF (49:32) - Zac’s cross-country bike ride (56:25) - Expectations vs. reality (58:57) - The coup attempt (01:01:59) - Tiring work (01:05:47) - Going to the White House (01:09:40) - DOGE & disrespect (01:12:54) - “We’re just getting started” (01:14:18) - Who OpenGov is hiring (and where) (01:15:13) - What “grit” means to Zac Mentioned in this episode: Joe Lonsdale, Cox Enterprises, OpenAI, the Department of Government Efficiency, Workday, H.R. McMaster, Stanford University, Formation 8, 8VC, the National Academy of Sciences, the Stanford Review, Kamala Harris, Marc Andreessen, Balaji Srinivasan, Coinbase, Earn, Ben Horowitz, Facebook, Steve Laughlin, Cisco, Laurene Powell Jobs, Glynn Capital, Acme, Allen & Company, Harry You, Joe Tucci, EMC, Bill Green, Accenture, Tyler Technologies, HP, Josh Kushner, GTY Technology Holdings, John Keker, Palantir, CKAN, Oracle, Kevin McCarthy, The American Technology Council Summit, Jeff Bezos, Tim Cook, Satya Nadella, Pat Gelsinger, Donald Trump, Jared Kushner, Elon Musk, Bill Clinton, and Al Gore.Links:Connect with ZacLinkedInConnect with JoubinTwitterLinkedInEmail: [email protected] Learn more about Kleiner PerkinsThis episode was edited by Eric Johnson from LightningPod.fm

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ABOUT THIS SHOW

Grit explores what it takes to create, build, and scale world-class organizations. It features weekly episodes highlighting the leaders who are pushing their companies to make a difference. This series is hosted by Joubin Mirzadegan, go to market operating partner at Kleiner Perkins, a venture capital firm investing in history-making founders.

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Kleiner Perkins

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