Bret Taylor, every mention

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every year anyone Harry Stebbings 57Jason Lemkin 11Cliff Weitzman 11Reggie Marable 8Clay Bavor 7Rory O'Driscoll 4Zico Kolter 2Everett Randle 2Adam Mosseri 2Paul Buchheit 1

Verbatim, from the transcripts: the passages where Bret Taylor comes up

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Jensen Huang Declares AGI Has Arrived | Tesla Launches Cybercabs | Index Pulls Out of Town Sep 10, 2026 · 2 mentions

  • ▶ 1:13:40 Harry Stebbings I think everyone in this category is being forced to, though, by Brett Taylor, who's being very clear in terms of his expansion, and. 2 times in the scene

How to Build Your Own Data Center & Why Every Startup Should Do It Sep 5, 2026 · 15 mentions

Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need · 20VC with Harry Stebbings Jul 4, 2026 · 25 mentions

  • ▶ 1:37 Harry Stebbings Um, so I want to start with, I heard that Brett tried to hire you or start a company with you several times before Sierra. 3 times in the scene
  • ▶ 22:30 Harry Stebbings What's your personal take and what are you and Brett sit around the fire and say, should you put a cap on this?
  • ▶ 26:30 Clay Bavor So Brett and I are constantly building agents ourselves. 3 times in the scene
  • ▶ 39:57 Clay Bavor So Brett and I write a usually six to 10 page memo.
  • ▶ 42:06 Harry Stebbings You and Brett, I mean, like, it's the dream team of the best of the best operators. 6 times in the scene
  • ▶ 50:13 Clay Bavor Each of our values comes directly from Brett and me, and actually one of the best decisions we made was, I think it was the time we were five or six employees. 3 times in the scene
  • ▶ 59:46 Harry Stebbings What was the most recent disagreement you and Brett had? 2 times in the scene
  • ▶ 1:00:59 Harry Stebbings What when Brett says something, are you like, yep, I'm sure he's a G at that. 6 times in the scene

Anthropic's Fable Banned by US Government | Wix & Adobe Hit All-Time Lows | Mistral Raising at $20BN · 20VC with Harry Stebbings Jun 18, 2026 · 2 mentions

  • ▶ 1:12:47 unnamed speaker I mean, you know, Brett, you guys know so much better than me. 2 times in the scene

Anthropic's Raise & What It Means for Potential IPO? Mag7: Google & Amazon Up, Meta & Microsoft Down · 20VC with Harry Stebbings May 7, 2026 · 8 mentions

  • ▶ 30:25 Rory O'Driscoll In other words, Brett Taylor can call higher than anyone else.
  • ▶ 1:10:56 Harry Stebbings Um, uh, speaking of, uh, OpenAI, OpenAI's chairman, Brett Taylor, is out in market raising nine hundred and fifty million dollars
  • ▶ 1:11:49 Jason Lemkin Um, and I believe that these agents, you know, everyone from Brett Taylor to Owen at Intercom, everyone sees these agents, um, merging and they're going to do sales and CX and enterprise. 3 times in the scene
  • ▶ 1:16:26 Harry Stebbings The point is also on the flip side, OpenAI would buy them today for 40, fifty billion to get Brett as CEO. 3 times in the scene

OpenAI Kills Sora & Hits $100M ARR on Ads | Oura Going Public & Whoop Raises at $10BN · 20VC with Harry Stebbings Apr 2, 2026 · 1 mention

  • ▶ 15:36 Harry Stebbings It's the best thing for OpenAI not to buy Sierra, incorporate that as a customer support product, and have Brett Taylor come in as the day-to-day CEO, and Sam can be fundraiser, Sam can be master of...

Anthropic vs The Pentagon: Who Wins? | The Data Center Arms Race | The Ultimate Stock Picks · 20VC with Harry Stebbings Mar 12, 2026 · 1 mention

  • ▶ 48:35 Jason Lemkin And if you're best at digital transformation for enterprises, maybe that's what Brett Taylor is.

Anthropic vs The Pentagon: Who Wins? | OpenAI's $110BN Mega Round | Cursor Hits $2BN in ARR · 20VC with Harry Stebbings Mar 5, 2026 · 2 mentions

  • ▶ 29:28 unnamed speaker Brett Taylor would be in charge, right? 2 times in the scene

Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded? · 20VC with Harry Stebbings Feb 12, 2026 · 1 mention

  • ▶ 56:37 Harry Stebbings Mike, Mark, and the 14 companies in the last two years that raised over a hundred million dollars with Brett from Sierra, I don't think that's a good place to be investing.

20VC: From $6.2BN Market Cap to $2.8BN: What Is Not Translating About Navan's Public Story | Are Any Public Company CEOs Actually Happy? | Why Navan Built It's Own Customer Service AI and What it Could Mean For Customer Service AI with Ariel Cohen Feb 7, 2026 · 1 mention

  • ▶ 20:48 Harry Stebbings Why did you decide to do a build versus buy and work with a Brat Taylor at Sierra or a Jesse at Dakagon?

Harvey CEO Winston Weinberg: How to Make Mega Deals | Lessons from Rabois, Halligan & Grady · 20VC with Harry Stebbings Jan 19, 2026 · 1 mention

  • ▶ 33:50 Harry Stebbings This is what I worry about, though, when I look at kind of, when you look at GRR figures, and you think about like a Sierra, and it's like the growth, and Brett's amazing, and like the best of the best, Jesus, like, take my money too,…

a16z's David George on the Most Controversial Bet at a16z & Do Margins and Revenue Matter in AI? · 20VC with Harry Stebbings Dec 15, 2025 · 1 mention

Anthropic Raises $30B from Microsoft & NVIDIA & NVIDIA’s Core Business Faces TPU Threat · 20VC with Harry Stebbings Nov 27, 2025 · 6 mentions

Benchmark's GP, Everett Randle on Why Mega Funds Will Not Produce Good Returns · 20VC with Harry Stebbings Nov 10, 2025 · 2 mentions

  • ▶ 36:32 Everett Randle You know, more than Brett Taylor, who represents this wave of AI applications. 2 times in the scene

Is a $4.5BN Exit Enough in VC? & Harvey Raises $150M & Why Google is a Buy and Amazon is a Sell · 20VC with Harry Stebbings Nov 6, 2025 · 2 mentions

OpenAI Restructuring: Who Wins and Who Loses & Mercor Raises $350M at a $10BN Valuation · 20VC with Harry Stebbings Oct 30, 2025 · 3 mentions

  • ▶ 7:57 unnamed speaker And then the final winner, I just got to say, and I notice a lot, but Brett Taylor just wins the best board chairman of the year award again.
  • ▶ 14:17 unnamed speaker Master corporate financier like Taylor and Sam Altman on your side. 2 times in the scene

Why VC Today is Worse than 2021 · 20VC with Harry Stebbings Oct 23, 2025 · 1 mention

Thinking Machines Co-Founder Joins Meta for $3.5BN, Industry Venture's $665M Acquisition · 20VC with Harry Stebbings Oct 16, 2025 · 1 mention

  • ▶ 51:07 unnamed speaker I mean, I think Brett Taylor is an example of someone at the high end.

Are Burn Multiples BS in an AI World? & Sam Altman Needs $1TRN of Energy · 20VC with Harry Stebbings Oct 2, 2025 · 1 mention

  • ▶ 33:08 Harry Stebbings I also think, by the way, that Alex Wang's acquisition created this very dangerous precedent in venture investors' minds where they're like, well, if Alex is worth 14, Brett Taylor's worth 30, and then Iliad's worth 30, and then Mira's…

20VC: Why 90% of Founders Build Startups Wrong | Why AI Growth Rates are Sustainable & Remote Work is BS and the AI Talent War | Competing with Brett Taylor and Sierra: Who Wins the Customer Service War with Jesse Zhang, Decagon Sep 19, 2025 · 3 mentions

OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings Sep 11, 2025 · 9 mentions

  • ▶ 24:35 Harry Stebbings When we look at like a Brex, last round was thirteen billion, now seven hundred million growing 50%, and then you look at a Sierra, ok, I love Brett Taylor, phenomenal operator, interviewed him before, to not compete with Brett Taylor was… 2 times in the scene
  • ▶ 25:19 Jason Lemkin The, the, the, the, the, the hundred X, but I think, I mean, Brett Taylor, if you buy Sierra, you get everything, right? 5 times in the scene
  • ▶ 36:46 Jason Lemkin Look at Brett Taylor.
  • ▶ 1:07:29 Jeff Lawson Yeah, because if I, let's say you're Brett at Salesforce selling you contact center automation, and they've got Service Cloud, which is, from memory, a third of their revenue or whatever, right?

Why Apple Needs a Management Overhaul & Why Google is Catching Up with Hyperscalers · 20VC with Harry Stebbings Jul 31, 2025 · 1 mention

Figma’s IPO: The Full Breakdown & Why Melio’s $2.5BN Acquisition is “Discouraging” · 20VC with Harry Stebbings Jul 3, 2025 · 1 mention

  • ▶ 37:38 Jason Lemkin Anything incentives are hard, but I mean, Zach made it work with Brett Taylor, right?

Chime IPO: Are IPOs Hotter Than Ever? · 20VC with Harry Stebbings Jun 19, 2025 · 3 mentions

  • ▶ 11:03 unnamed speaker Well, I'll tell you, if I had to simplify it, I think the question is, is, um, Alexander Wang as good or better than Brett Taylor? 3 times in the scene

Rippling vs. Deel Lawsuit: WTF Happens Now? The Future of the Late Stage Private Market · 20VC with Harry Stebbings May 22, 2025 · 1 mention

Benchmark vs a16z: Why Stage Specific Firms Win · 20VC with Harry Stebbings May 8, 2025 · 1 mention

20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI May 2, 2025 · 11 mentions

  • ▶ 0:10 Harry Stebbings Today we have one of the best, Head of Global Sales for one of the fastest growing AI companies in the world, Sierra, founded by Brett Taylor and funded by Benchmark and Greenos.
  • ▶ 7:19 Reggie Marable So I consider Brett one of the, I call him the apex predator. 5 times in the scene
  • ▶ 19:47 Reggie Marable Some of these are going to be, you know, the next wave of Brett Taylors are going to be some of these agent product managers.
  • ▶ 31:28 Harry Stebbings A question that I have for you is, are you a unique situation respectfully because you're Brett Taylor and the team is so stellar? 2 times in the scene
  • ▶ 49:11 Reggie Marable And what's really cool is our co-founder, Brett and Clay, they, they, uh, heavily involved in like meeting with customers. 2 times in the scene

Benchmark GP, Victor Lazarte: The 3 Traits All the Best Founders Have · 20VC with Harry Stebbings Apr 14, 2025 · 6 mentions

Eric Vishria: Where is the Value in AI - Chips, Models or Apps? | E1206 · 20VC with Harry Stebbings Sep 25, 2024 · 1 mention

Zico Kolter: OpenAI's Newest Board Member on The Biggest Questions and Concerns in AI Safety | E1197 · 20VC with Harry Stebbings Sep 4, 2024 · 2 mentions

  • ▶ 1:00:50 Zico Kolter Um, I got, actually the, the, the, the day before I started as department head, I got an email from, from, from Brett, the chair of the board, just saying, hey, do you want to talk about maybe joining the OpenAI board? 2 times in the scene

Reid Hoffman: The Future of TikTok and The Inflection AI Deal | E1163 · 20VC with Harry Stebbings Jun 10, 2024 · 1 mention

Adam Mosseri: Why Video Is Bad For Business; Does Feed Matter Anymore? | E1039 · 20VC with Harry Stebbings Jul 24, 2023 · 2 mentions

  • ▶ 3:44 Adam Mosseri And then, Brett Taylor was my boss, and I was the director of design for Mobile. 2 times in the scene

20VC: Y Combinator's Paul Buchheit on Creating Gmail Version 1.0 & Leadership Lessons from Working With Zuckerberg and Larry Paige Nov 1, 2017 · 1 mention

  • ▶ 25:21 Paul Buchheit And actually, to be clear, it was my co-founder, Brett Taylor, who really did the work on that.
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