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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