Grit

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

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

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

Guest: Bret Taylor, Co-Founder of Sierra

Chapters:
00:00 Trailer
00:49 Introduction
01:57 Saving OpenAI
09:15 Overwhelming yet capable of a lot
13:36 Father and founder
16:49 History is written by the victors
22:13 How you price matters
35:58 Stickiest piece of software
49:48 The first realtime social network
55:34 Facebook CTO who rewrote Google Maps
1:02:10 Least known, most impressive
1:11:39 The best way to predict the future
1:16:22 Most personally passionate
1:21:22 Currency of reputation
1:27:17 Away from work
1:28:35 Who Sierra is hiring
1:28:58 What “grit” means to Bret
1:29:18 Outro

Mentioned 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 Collison

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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 Aurora

Chapters:
00:00 Trailer
00:43 Introduction
01:59 FSD: are we there?
14:31 The competition, a million dollar check from LA to LV
22:50 Dream like an amateur, execute like a pro
32:30 Operate with integrity
42:49 The future is here, unevenly distributed
49:36 Underestimated decisions, minimizing regrets
1:03:55 Retaining value
1:16:45 Integrating self-driving
1:28:20 Lifer
1:29:25 Who Aurora is hiring
1:29:53 What “grit” means to Chris
1:30:15 Outro

Mentioned 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 Khosrowshahi

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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 & CEO

Chapters: 

00:00 Trailer

00:45 Introduction

01:45 Track record, relationships, trust

13:21 Acquisitions every year

17:32 Product-focused

24:40 Family, dyslexia, and without shame

30:46 Wang Laboratories

35:59 Ready being CEO

40:17 Reinventing your business

50:08 Numbers don’t lie

54:09 Sales calls and making mistakes

56:20 Adapting leadership style

1:06:32 Best leadership year ever

1:13:35 A busy, exhausting schedule

1:22:07 Candid with me

1:25:21 What “grit” means to John

1:26:43 Outro

Mentioned 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 Selcher

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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 Trailer
00:47 Introduction
03:00 Huge company, taking the long view
10:28 Market cap shift to big tech
14:44 The data infrastructure opportunity
20:30 Massive economic opportunity
31:33 Semiconductor industry and geopolitics
40:46 Taiwan and Moore’s Law
44:05 Getting hammered down 50%
47:05 Silicon Valley
51:15 All in despite risks
55:37 The CEO checkbox
1:01:22 Email from Matt, subject: Grit
1:07:35 The higher you go
1:15:44 Who Marvell is hiring
1:20:14 What “grit” means to Matt
1:24:40 Outro

Mentioned 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 Koopmans

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

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

Chapters:
00:00 Trailer
00:52 Introduction
02:22 Fire in my belly
10:06 Constraints
12:19 Peak performance
16:38 Helping while in sheer panic
21:43 The general ethos
30:14 Customer value
36:08 Excited and scared
47:25 Becoming CEO
54:19 Feeling behind
1:01:51 Very lonely
1:05:34 Losing credibility
1:08:42 Slowing down, sitting still
1:12:31 No patience to finish a book
1:15:39 Who HubSpot is hiring
1:15:54 What “grit” means to Yamini
1:16:45 Outro

Mentioned 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 Humankind

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

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

Chapters:
00:00 Trailer
00:53 Introduction
01:40 Family, wealth, class
14:40 Happiness disparity and longevity
19:25 I need more to give away more
25:04 The relentless fundraiser
33:53 Kids and travel
36:06 No track record, the great white buffalo
38:59 Business and politics
43:53 Fired from Washington
45:52 Fundraising, presidents, podcast guests
48:04 Private equity and sports
53:44 Expenses — no charges
55:49 Waking up with energy
57:26 Preserving copies
1:02:05 Organizational architecture
1:03:41 Bury me in my plane
1:08:11 Not a big luxury spender
1:10:32 What “grit” means to David
1:10:50 Outro

Mentioned 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 McCartney

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X: @Joubinmir

LinkedIn: Joubin Mirzadegan
Email: [email protected]

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Amplitude helped define the modern analytics stack, powering digital products with deep behavioral insights. But in a world shifting toward agentic interfaces and vertically integrated AI, even a category leader has to evolve.

In this episode, CEO Spenser Skates shares how he’s rethinking AI within the constraints of a 13-year-old codebase, why analytics remains Amplitude’s competitive edge—and why taking the company public early was a risk worth taking.

Chapters:
00:00 Trailer
00:43 Introduction
01:26 AI is still very early
05:48 The urgency of building from the ground up
08:49 Bringing in new blood
11:23 Higher valuations and going public
15:00 Who’s leading who
18:39 Markets being open and closed
21:14 Being the incumbent in AI
24:40 Slow innovation
31:43 The ultimate founder
37:06 Things willing to relinquish
44:04 Being the person I want to be
46:41 Between family and work
50:08 Becoming the person you hate
55:16 Chief general, chief justice, chief priest
1:02:56 Tired founders
1:04:32 Missing out
1:14:51 Who Amplitude is hiring
1:15:41 What Spenser means to Spenser
1:16:54 Outro

Mentioned 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 Jordan

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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 Trailer
00:31 Introduction
02:07 Meeting smart people, seeing the world
03:40 Eroded margins
09:52 Charismatic and overconfident
15:32 Not an overnight decision
20:08 The founder has returned
23:10 Redoing the hiring
26:38 No substitute for passion
31:00 Working for and with my brother
37:28 Working with forwarders
42:14 Being a founder can be lonely
47:49 Life’s work
54:06 The right person for the job
1:00:55 19 countries
1:04:57 Blowing people up
1:07:24 Work and being a good dad
1:08:34 Not doing it for money and loving money
1:17:52 Import and export tariffs
1:22:57 De minimis
1:25:54 Panama and the Suez Canal
1:36:50 Going public
1:42:24 Who Flexport is Hiring
1:42:42 What "grit" means to Ryan
1:43:06 Outro

Mentioned 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, Airbnb

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Guest: Pedro Franceschi

Pedro Franceschi is the co-founder and CEO of Brex, a fintech company reshaping how businesses manage their finances.

Originally from Brazil, Pedro went from teenage hacker to leading one of the most well-known names in modern financial technology—building a platform trusted by startups and enterprises alike.

In this episode, Pedro shares what it took to launch “Brex 3.0,” why he moved to a single-CEO model, and how tough structural changes set the stage for leaner, faster growth.

Chapters:
00:00 Trailer
00:46 Introduction
01:45 Startup roller coaster
05:21 Founders know how to have fun
07:12 Belief barrier evolution
12:00 Early state of life in Brazil
13:23 Controlling variables
15:32 Screen time
19:23 Making small decisions
23:27 Learning raises the bar
26:15 People manager
38:49 Getting underwater
42:05 Growth accelerated
47:51 Vision from the top down
52:13 Leadership organization
54:01 AI software engineering physics
54:43 People complain about change
59:42 Believers and non-believers
1:04:09 Equity and bonus controversy
1:08:40 Big swings and going public
1:14:15 Control in unpredictability
1:18:04 Living in a pixel

1:19:52 Meditate, sleep, diet, exercise

1:24:36 Mental health and stress
1:33:12 Who Brex is hiring
1:33:49 What "grit" means to Pedro
1:34:39 Outro

Mentioned 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.

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This episode was produced by Kleiner Perkins and edited by IQvideo.

The trailer and distribution for this episode were handled by Atomik Growth.

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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 Trailer
00:42 Introduction
01:21 His fifth company
04:26 Entrepreneurs’ existential fear
10:53 Customer engagement and new innovations
12:46 No private jets, no business class
19:34 “I never used money”
23:38 Born and raised in India
26:17 Hiring legends
30:35 Walking on water
35:09 “Dolphining”
39:55 Areas of weakness
42:11 Passionate even on the weekends
44:56 Work during roller coasters
47:35 The weight of the world is on your shoulders
49:21 Leveraging AI
56:20 Outro

Mentioned 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), security

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