CRO/CSO Dialpad, Dan O’Connell: Taking Risks and Running a Company

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: grit@kleinerperkins.comLearn more about Kleiner Perkins

19 Touko 1h 27min

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: grit@kleinerperkins.comLearn more about Kleiner Perkins

12 Touko 1h 25min

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: grit@kleinerperkins.comLearn more about Kleiner Perkins

5 Touko 1h 17min

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: grit@kleinerperkins.comkleinerperkins.com

28 Huhti 1h 11min

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: grit@kleinerperkins.comLearn more about Kleiner Perkins

21 Huhti 1h 17min

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: grit@kleinerperkins.comLearn more about Kleiner Perkins

14 Huhti 1h 43min

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: grit@kleinerperkins.comThis 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

7 Huhti 1h 35min

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: grit@kleinerperkins.com Learn more about Kleiner Perkins

31 Maalis 56min